JP4760209B2 - Method for producing pyrimidine compound - Google Patents
Method for producing pyrimidine compound Download PDFInfo
- Publication number
- JP4760209B2 JP4760209B2 JP2005231687A JP2005231687A JP4760209B2 JP 4760209 B2 JP4760209 B2 JP 4760209B2 JP 2005231687 A JP2005231687 A JP 2005231687A JP 2005231687 A JP2005231687 A JP 2005231687A JP 4760209 B2 JP4760209 B2 JP 4760209B2
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidine
- ethylidenehydrazino
- propyl
- butylphenyl
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、ピリミジン化合物の製造方法に関する。 The present invention relates to a method for producing a pyrimidine compound.
式(4)
で示されるピリミジン化合物は、例えばいもち病、紋枯病、小球菌核病、ごま葉枯病、白葉枯病等のイネの各種病害や例えば胡瓜灰色疫病、菜豆菌核病、苺灰色黴病等の野菜、果樹の各種病害の予防および治療剤として有効であることが知られている(例えば特許文献1および2参照。)。 Formula (4)
(Wherein R 1 represents a hydrogen atom or a lower alkyl group, and R 2 and R 3 are the same or different and represent a lower alkyl group.)
The pyrimidine compounds represented by are various diseases of rice such as rice blast, coat blight, staphylococcal nuclear disease, sesame leaf blight, white leaf blight, etc. It is known to be effective as a preventive and therapeutic agent for various diseases of vegetables and fruit trees (see, for example, Patent Documents 1 and 2).
かかる式(4)で示されるピリミジン化合物の製造方法としては、例えば式(2)
で示されるアミジノヒドラゾン化合物と式(3)
(式中、R2およびR3は上記と同一の意味を表わす。)
で示されるβ−ジケトン化合物とを、そのままもしくは有機溶媒中で反応させる方法が知られている(例えば特許文献1参照。)が、その収率は75%程度であり、必ずしも工業的に充分満足し得る製造方法とは言えなかった。 As a method for producing the pyrimidine compound represented by the formula (4), for example, the formula (2)
(Wherein R 1 represents the same meaning as described above.)
And an amidinohydrazone compound represented by the formula (3)
(Wherein R 2 and R 3 represent the same meaning as described above.)
Is known (for example, refer to Patent Document 1), but the yield is about 75%, and it is always sufficiently industrially satisfactory. It was not a possible manufacturing method.
このような状況のもと、本発明者らは、上記式(4)で示されるピリミジン化合物をより収率良く製造できる方法を開発すべく検討したところ、アミノグアニジンの塩酸塩と式(1)
で示されるアセトフェノン化合物とを、水中で反応させて、式(2)
(式中、R1は上記と同一の意味を表わす。)
で示されるアミジノヒドラゾン化合物の塩酸塩を得、得られた式(2)で示されるアミジノヒドラゾン化合物の塩酸塩と上記式(3)で示されるβ−ジケトン化合物とを、水中、pH7〜9の範囲で反応させることにより、式(4)で示されるピリミジン化合物を、良好な収率で製造することができることを見出し、本発明に至った。 Under such circumstances, the present inventors studied to develop a method capable of producing the pyrimidine compound represented by the above formula (4) with higher yield. As a result, the aminoguanidine hydrochloride and the formula (1)
(Wherein R 1 represents the same meaning as described above.)
Is reacted with an acetophenone compound represented by the formula (2):
(Wherein R 1 represents the same meaning as described above.)
The hydrochloride of the amidinohydrazone compound represented by formula (2) and the β-diketone compound represented by the formula (3) obtained above in water were adjusted to pH 7-9. By reacting in the range, it was found that the pyrimidine compound represented by the formula (4) can be produced in good yield, and the present invention has been achieved.
すなわち、本発明は、アミノグアニジンの塩酸塩と式(1)
で示されるアセトフェノン化合物とを、水中で反応させて、式(2)
(式中、R1は上記と同一の意味を表わす。)
で示されるアミジノヒドラゾン化合物の塩酸塩を得、得られた式(2)で示されるアミジノヒドラゾン化合物の塩酸塩と式(3)
(式中、R2およびR3はそれぞれ同一または相異なって、低級アルキル基を表わす。)で示されるβ−ジケトン化合物とを、水中、pH7〜9の範囲で反応させることを特徴とする式(4)
(式中、R1、R2およびR3は上記と同一の意味を表わす。)
で示されるピリミジン化合物の製造方法を提供するものである。 That is, the present invention provides aminoguanidine hydrochloride and formula (1)
(In the formula, R 1 represents a hydrogen atom or a lower alkyl group.)
Is reacted with an acetophenone compound represented by the formula (2):
(Wherein R 1 represents the same meaning as described above.)
The hydrochloride of the amidinohydrazone compound represented by formula (2) was obtained, and the hydrochloride of the amidinohydrazone compound represented by formula (2) and formula (3) were obtained.
(Wherein R 2 and R 3 are the same or different and each represents a lower alkyl group) and a β-diketone compound represented by the formula (I) is reacted in water within a pH range of 7-9. (4)
(In the formula, R 1 , R 2 and R 3 have the same meaning as described above.)
The manufacturing method of the pyrimidine compound shown by these is provided.
本発明によれば、イネ、野菜、果樹等の各種病害の予防および治療剤として有効な式(4)で示されるピリミジン化合物を、より収率よく製造することができる。 According to the present invention, a pyrimidine compound represented by the formula (4) effective as a preventive and therapeutic agent for various diseases such as rice, vegetables, fruit trees, etc. can be produced with higher yield.
まず、アミノグアニジンの塩酸塩と式(1)
で示されるアセトフェノン化合物(以下、アセトフェノン化合物(1)と略記する。)とを、水中で反応させて、式(2)
(式中、R1は上記と同一の意味を表わす。)
で示されるアミジノヒドラゾン化合物の塩酸塩(以下、アミジノヒドラゾン化合物の塩酸塩(2)と略記する。)を得る工程について説明する。 First, aminoguanidine hydrochloride and formula (1)
(In the formula, R 1 represents a hydrogen atom or a lower alkyl group.)
Is reacted with an acetophenone compound represented by the formula (hereinafter abbreviated as acetophenone compound (1)) in the formula (2).
(Wherein R 1 represents the same meaning as described above.)
The step of obtaining the hydrochloride of the amidinohydrazone compound shown below (hereinafter abbreviated as hydrochloride (2) of the amidinohydrazone compound) will be described.
アミノグアニジンの塩酸塩は、通常市販のものが用いられる。また、フリー体のアミノグアニジンと塩酸とを混合することにより調製したアミノグアニジンの塩酸塩を用いてもよいし、例えばアミノグアニジンの炭酸塩等のアミノグアニジンの塩酸塩以外の酸付加塩と塩酸とを混合することにより調製したアミノグアニジンの塩酸塩を用いてもよい。 Commercially available aminoguanidine hydrochloride is usually used. Alternatively, aminoguanidine hydrochloride prepared by mixing free aminoguanidine and hydrochloric acid may be used, for example, acid addition salts other than aminoguanidine hydrochloride such as aminoguanidine carbonate and hydrochloric acid. Aminoguanidine hydrochloride prepared by mixing may be used.
アセトフェノン化合物(1)の式中、R1は水素原子または低級アルキル基を表わす。低級アルキル基としては、例えばメチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基等の炭素数1〜4のアルキル基が挙げられる。 In the formula of the acetophenone compound (1), R 1 represents a hydrogen atom or a lower alkyl group. Examples of the lower alkyl group include alkyl groups having 1 to 4 carbon atoms such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, and tert-butyl group. It is done.
かかるアセトフェノン化合物(1)としては、例えばアセトフェノン、2’−メチルアセトフェノン、2’−エチルアセトフェノン、2’−n−プロピルアセトフェノン、2’−イソプロピルアセトフェノン、2’−n−ブチルアセトフェノン、2’−イソブチルアセトフェノン、2’−sec−ブチルアセトフェノン、2’−tert−ブチルアセトフェノン、3’−メチルアセトフェノン、3’−エチルアセトフェノン、3’−n−プロピルアセトフェノン、3’−イソプロピルアセトフェノン、3’−n−ブチルアセトフェノン、3’−イソブチルアセトフェノン、3’−sec−ブチルアセトフェノン、3’−tert−ブチルアセトフェノン、4’−メチルアセトフェノン、4’−エチルアセトフェノン、4’−n−プロピルアセトフェノン、4’−イソプロピルアセトフェノン、4’−n−ブチルアセトフェノン、4’−イソブチルアセトフェノン、4’−sec−ブチルアセトフェノン、4’−tert−ブチルアセトフェノン等が挙げられる。かかるアセトフェノン化合物(1)は、通常市販されているものが用いられる。 Examples of the acetophenone compound (1) include acetophenone, 2′-methylacetophenone, 2′-ethylacetophenone, 2′-n-propylacetophenone, 2′-isopropylacetophenone, 2′-n-butylacetophenone, 2′-isobutyl. Acetophenone, 2′-sec-butylacetophenone, 2′-tert-butylacetophenone, 3′-methylacetophenone, 3′-ethylacetophenone, 3′-n-propylacetophenone, 3′-isopropylacetophenone, 3′-n-butyl Acetophenone, 3′-isobutylacetophenone, 3′-sec-butylacetophenone, 3′-tert-butylacetophenone, 4′-methylacetophenone, 4′-ethylacetophenone, 4′-n-propylacetate Phenone, 4'-isopropyl acetophenone, 4'-n-butyl-acetophenone, 4'-isobutyl acetophenone, 4'-sec-butyl-acetophenone, 4'-tert-butyl-acetophenone, and the like. As the acetophenone compound (1), a commercially available product is usually used.
アセトフェノン化合物(1)の使用量は、アミノグアニジンの塩酸塩に対して、通常0.9〜5モル倍、好ましくは0.95〜2モル倍である。 The usage-amount of an acetophenone compound (1) is 0.9-5 mol times normally with respect to the hydrochloride of aminoguanidine, Preferably it is 0.95-2 mol times.
水の使用量は、アミノグアニジンの塩酸塩に対して、通常1〜20重量倍、好ましくは3〜15重量倍である。 The amount of water used is usually 1 to 20 times by weight, preferably 3 to 15 times by weight, based on the hydrochloride of aminoguanidine.
反応温度は、通常0〜100℃、好ましくは40〜80℃である。 The reaction temperature is usually 0 to 100 ° C, preferably 40 to 80 ° C.
アミノグアニジンの塩酸塩とアセトフェノン化合物(1)との反応は、通常水中で、その両者を接触、混合させることにより実施され、その混合順序は特に制限されない。 The reaction between the aminoguanidine hydrochloride and the acetophenone compound (1) is usually carried out by contacting and mixing the two in water, and the mixing order is not particularly limited.
また、反応を阻害しない範囲で、有機溶媒を共存させて反応を行ってもよく、かかる有機溶媒としては、例えばメタノール、エタノール、n−プロパノール、イソプロパノール、n−ブタノール、メチルセルソルブ、エチルセルソルブ等のアルコール系溶媒、例えばジエチルエーテル、テトラヒドロフラン、ジオキサン、ジメトキシエタン等のエーテル系溶媒、例えばアセトン、メチルエチルケトン等のケトン系溶媒、例えばトルエン、キシレン等の芳香族炭化水素系溶媒等が挙げられる。 In addition, the reaction may be carried out in the presence of an organic solvent as long as the reaction is not inhibited. Examples of the organic solvent include methanol, ethanol, n-propanol, isopropanol, n-butanol, methyl cellosolve, ethyl cellosolve. And alcohol solvents such as diethyl ether, tetrahydrofuran, dioxane and dimethoxyethane, ketone solvents such as acetone and methyl ethyl ketone, and aromatic hydrocarbon solvents such as toluene and xylene.
反応終了後、例えば反応液を冷却した後、濾過処理することにより、アミジノヒドラゾン化合物の塩酸塩(2)を取り出すことができる。取り出したアミジノヒドラゾン化合物の塩酸塩(2)は、例えば再結晶等の通常の精製手段によりさらに精製してもよい。また、アミジノヒドラゾン化合物の塩酸塩(2)を取り出すことなく、アミジノヒドラゾン化合物の塩酸塩(2)を含む反応液をそのまま後述する反応に用いてもよい。 After completion of the reaction, for example, the reaction solution is cooled and then filtered, whereby the hydrochloride (2) of the amidinohydrazone compound can be taken out. The extracted hydrochloride (2) of the amidinohydrazone compound may be further purified by ordinary purification means such as recrystallization. Moreover, you may use the reaction liquid containing hydrochloride (2) of an amidinohydrazone compound as it is for the reaction mentioned later, without taking out hydrochloride (2) of an amidinohydrazone compound.
かかるアミジノヒドラゾン化合物の塩酸塩(2)としては、例えば1−フェニルエチリデンアミノグアニジンの塩酸塩、1−(2−メチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(2−エチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(2−n−プロピルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(2−イソプロピルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(2−n−ブチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(2−イソブチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(2−sec−ブチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(2−tert−ブチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(3−メチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(3−エチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(3−n−プロピルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(3−イソプロピルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(3−n−ブチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(3−イソブチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(3−sec−ブチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(3−tert−ブチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(4−メチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(4−エチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(4−n−プロピルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(4−イソプロピルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(4−n−ブチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(4−イソブチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(4−sec−ブチルフェニル)エチリデンアミノグアニジンの塩酸塩、1−(4−tert−ブチルフェニル)エチリデンアミノグアニジンの塩酸塩等が挙げられる。 Examples of the hydrochloride (2) of the amidinohydrazone compound include 1-phenylethylideneaminoguanidine hydrochloride, 1- (2-methylphenyl) ethylideneaminoguanidine hydrochloride, and 1- (2-ethylphenyl) ethylideneaminoguanidine. 1- (2-n-propylphenyl) ethylideneaminoguanidine hydrochloride, 1- (2-isopropylphenyl) ethylideneaminoguanidine hydrochloride, 1- (2-n-butylphenyl) ethylideneaminoguanidine Hydrochloride, hydrochloride of 1- (2-isobutylphenyl) ethylideneaminoguanidine, hydrochloride of 1- (2-sec-butylphenyl) ethylideneaminoguanidine, hydrochloric acid of 1- (2-tert-butylphenyl) ethylideneaminoguanidine Salt, 1- (3-methylphenyl) Ethylideneaminoguanidine hydrochloride, 1- (3-ethylphenyl) ethylideneaminoguanidine hydrochloride, 1- (3-n-propylphenyl) ethylideneaminoguanidine hydrochloride, 1- (3-isopropylphenyl) ethylideneaminoguanidine Of 1- (3-n-butylphenyl) ethylideneaminoguanidine hydrochloride, 1- (3-isobutylphenyl) ethylideneaminoguanidine hydrochloride, 1- (3-sec-butylphenyl) ethylideneaminoguanidine 1- (3-tert-butylphenyl) ethylideneaminoguanidine hydrochloride, 1- (4-methylphenyl) ethylideneaminoguanidine hydrochloride, 1- (4-ethylphenyl) ethylideneaminoguanidine hydrochloride, 1- (4-n-propylphenyl) Tylideneaminoguanidine hydrochloride, 1- (4-isopropylphenyl) ethylideneaminoguanidine hydrochloride, 1- (4-n-butylphenyl) ethylideneaminoguanidine hydrochloride, 1- (4-isobutylphenyl) ethylideneamino Examples include guanidine hydrochloride, 1- (4-sec-butylphenyl) ethylideneaminoguanidine hydrochloride, 1- (4-tert-butylphenyl) ethylideneaminoguanidine hydrochloride, and the like.
続いて、得られたアミジノヒドラゾン化合物の塩酸塩(2)と式(3)
(式中、R1、R2およびR3は上記と同一の意味を表わす。)
で示されるピリミジン化合物(以下、ピリミジン化合物(4)と略記する。)を製造する工程について説明する。 Subsequently, hydrochloride (2) of the obtained amidinohydrazone compound and formula (3)
(Wherein R 2 and R 3 are the same or different and each represents a lower alkyl group) and a β-diketone compound (hereinafter abbreviated as β-diketone compound (3)), , Reaction in the range of pH 7-9, formula (4)
(In the formula, R 1 , R 2 and R 3 have the same meaning as described above.)
A process for producing a pyrimidine compound represented by (hereinafter abbreviated as pyrimidine compound (4)) will be described.
β−ジケトン化合物(3)の式中、R2およびR3はそれぞれ同一または相異なって、低級アルキル基を表わし、低級アルキル基としては、例えばメチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基等の炭素数1〜4のアルキル基が挙げられる。 In the formula of β-diketone compound (3), R 2 and R 3 are the same or different and each represents a lower alkyl group. Examples of the lower alkyl group include a methyl group, an ethyl group, an n-propyl group, and an isopropyl group. , N-butyl group, isobutyl group, sec-butyl group, tert-butyl group and other alkyl groups having 1 to 4 carbon atoms.
かかるβ−ジケトン化合物(3)としては、例えばペンタン−2,4−ジオン、ヘキサン−2,4−ジオン、ヘプタン−2,4−ジオン、オクタン−2,4−ジオン、ヘプタン−3,5−ジオン、オクタン−3,5−ジオン、ノナン−3,5−ジオン、ノナン−4,6−ジオン、デカン−4,6−ジオン等が挙げられる。かかるβ−ジケトン化合物(3)は、通常市販されているものが用いられる。 Examples of the β-diketone compound (3) include pentane-2,4-dione, hexane-2,4-dione, heptane-2,4-dione, octane-2,4-dione, heptane-3,5- Examples include dione, octane-3,5-dione, nonane-3,5-dione, nonane-4,6-dione, decane-4,6-dione, and the like. As the β-diketone compound (3), a commercially available product is usually used.
かかるβ−ジケトン化合物(3)の使用量は、アミジノヒドラゾン化合物の塩酸塩(2)に対して、通常0.9〜5モル倍、好ましくは1〜3モル倍である。 The amount of the β-diketone compound (3) used is usually 0.9 to 5 times, preferably 1 to 3 times the amount of the hydrochloride (2) of the amidinohydrazone compound.
アミジノヒドラゾン化合物の塩酸塩(2)とβ−ジケトン化合物(3)との反応は、その両者を、水中、pH7〜9の範囲で混合することにより実施され、好ましくはpH7.5〜8.5の範囲で混合することにより実施される。 The reaction of the hydrochloride (2) of the amidinohydrazone compound and the β-diketone compound (3) is carried out by mixing both of them in water within the range of pH 7 to 9, preferably pH 7.5 to 8.5. It is carried out by mixing in the range.
水の使用量は、アミジノヒドラゾン化合物の塩酸塩(2)に対して、通常0.1〜20重量倍、好ましくは1〜5重量倍である。上記で得られたアミジノヒドラゾン化合物の塩酸塩(2)を含む反応液をそのまま用いる場合には、該反応液中の水の量を考慮して、水の使用量を決めればよい。 The usage-amount of water is 0.1-20 weight times normally with respect to hydrochloride (2) of an amidinohydrazone compound, Preferably it is 1-5 weight times. When the reaction solution containing the hydrochloride (2) of the amidinohydrazone compound obtained above is used as it is, the amount of water used may be determined in consideration of the amount of water in the reaction solution.
反応を阻害しない範囲で、有機溶媒を共存させて反応を行ってもよく、かかる有機溶媒としては、例えばメタノール、エタノール、n−プロパノール、n−ブタノール、メチルセルソルブ、エチルセルソルブ等のアルコール系溶媒、例えばジエチルエーテル、テトラヒドロフラン、ジオキサン、ジメトキシエタン等のエーテル系溶媒、例えばトルエン、キシレン等の芳香族炭化水素系溶媒、例えばアセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン系溶媒が挙げられる。 The reaction may be carried out in the presence of an organic solvent as long as the reaction is not inhibited. Examples of the organic solvent include alcohols such as methanol, ethanol, n-propanol, n-butanol, methyl cellosolve, and ethyl cellosolve. Examples of the solvent include ether solvents such as diethyl ether, tetrahydrofuran, dioxane and dimethoxyethane, aromatic hydrocarbon solvents such as toluene and xylene, and ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone.
アミジノヒドラゾン化合物の塩酸塩(2)とβ−ジケトン化合物(3)との反応は、前記のとおり、pH7〜9、好ましくは7.5〜8.5の範囲で実施されるが、反応液のpH範囲をかかるpH範囲に調整するために、通常塩基が用いられる。塩基としては、例えば水酸化ナトリウム、水酸化カリウム等のアルカリ金属水酸化物、例えば炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩等が挙げられ、好ましくは、アルカリ金属炭酸塩が挙げられる。かかる塩基は、そのまま用いてもよいし、水溶液として用いてもよい。 The reaction of hydrochloride (2) of the amidinohydrazone compound and β-diketone compound (3) is carried out in the range of pH 7 to 9, preferably 7.5 to 8.5 as described above. In order to adjust the pH range to such a pH range, a base is usually used. Examples of the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, and preferably alkali metal carbonates. Such a base may be used as it is or as an aqueous solution.
反応温度は、通常0〜100℃、好ましくは40〜90℃である。 The reaction temperature is usually 0 to 100 ° C, preferably 40 to 90 ° C.
反応終了後、例えば反応液を冷却した後、濾過処理することにより、ピリミジン化合物(4)を取り出すことができる。 After completion of the reaction, for example, after cooling the reaction solution, the pyrimidine compound (4) can be taken out by filtration.
かくして得られるピリミジン化合物(4)としては、例えば4,6−ジメチル−2−(1−フェニルエチリデンヒドラジノ)ピリミジン、4−メチル−6−エチル−2−(1−フェニルエチリデンヒドラジノ)ピリミジン、4−メチル−6−n−プロピル−2−(1−フェニルエチリデンヒドラジノ)ピリミジン、4−メチル−6−n−ブチル−2−(1−フェニルエチリデンヒドラジノ)ピリミジン、4,6−ジエチル−2−(1−フェニルエチリデンヒドラジノ)ピリミジン、4−エチル−6−n−プロピル−2−(1−フェニルエチリデンヒドラジノ)ピリミジン、4−エチル−6−n−ブチル−2−(1−フェニルエチリデンヒドラジノ)ピリミジン、4,6−ジ−n−プロピル−2−(1−フェニルエチリデンヒドラジノ)ピリミジン、4−n−プロピル−6−n−ブチル−2−(1−フェニルエチリデンヒドラジノ)ピリミジン、4,6−ジメチル−2−[1−(2−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(2−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(2−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(2−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(2−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(2−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(2−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(2−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(2−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジメチル−2−[1−(2−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(2−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(2−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(2−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(2−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(2−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(2−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(2−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(2−エチルフェニル)エチリデンヒドラジノ]ピリミジン、 Examples of the pyrimidine compound (4) thus obtained include 4,6-dimethyl-2- (1-phenylethylidenehydrazino) pyrimidine, 4-methyl-6-ethyl-2- (1-phenylethylidenehydrazino) pyrimidine, 4-methyl-6-n-propyl-2- (1-phenylethylidenehydrazino) pyrimidine, 4-methyl-6-n-butyl-2- (1-phenylethylidenehydrazino) pyrimidine, 4,6-diethyl- 2- (1-phenylethylidenehydrazino) pyrimidine, 4-ethyl-6-n-propyl-2- (1-phenylethylidenehydrazino) pyrimidine, 4-ethyl-6-n-butyl-2- (1-phenyl) Ethylidenehydrazino) pyrimidine, 4,6-di-n-propyl-2- (1-phenylethylidenehydrazino) pyrimidine 4-n-propyl-6-n-butyl-2- (1-phenylethylidenehydrazino) pyrimidine, 4,6-dimethyl-2- [1- (2-methylphenyl) ethylidenehydrazino] pyrimidine, 4 -Methyl-6-ethyl-2- [1- (2-methylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-propyl-2- [1- (2-methylphenyl) ethylidenehydrazino] pyrimidine 4-methyl-6-n-butyl-2- [1- (2-methylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (2-methylphenyl) ethylidenehydrazino] pyrimidine 4-ethyl-6-n-propyl-2- [1- (2-methylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2 [1- (2-Methylphenyl) ethylidenehydrazino] pyrimidine, 4,6-di-n-propyl-2- [1- (2-methylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6 n-butyl-2- [1- (2-methylphenyl) ethylidenehydrazino] pyrimidine, 4,6-dimethyl-2- [1- (2-ethylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6 Ethyl-2- [1- (2-ethylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-propyl-2- [1- (2-ethylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl- 6-n-butyl-2- [1- (2-ethylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (2-ethylphenyl) ) Ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (2-ethylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- ( 2-ethylphenyl) ethylidenehydrazino] pyrimidine, 4,6-di-n-propyl-2- [1- (2-ethylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl- 2- [1- (2-ethylphenyl) ethylidenehydrazino] pyrimidine,
4,6−ジメチル−2−[1−(2−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(2−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(2−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(2−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(2−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(2−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(2−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(2−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(2−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジメチル−2−[1−(2−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(2−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(2−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(2−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(2−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(2−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(2−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(2−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(2−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、 4,6-dimethyl-2- [1- (2-n-propylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (2-n-propylphenyl) ethylidenehydrazino] Pyrimidine, 4-methyl-6-n-propyl-2- [1- (2-n-propylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [1- (2-n) -Propylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (2-n-propylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (2-n-propylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (2-n-propylphenyl) ethylidenehydrazino Pyrimidine, 4,6-di-n-propyl-2- [1- (2-n-propylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [1- (2 -N-propylphenyl) ethylidenehydrazino] pyrimidine, 4,6-dimethyl-2- [1- (2-isopropylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (2 -Isopropylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-propyl-2- [1- (2-isopropylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [ 1- (2-Isopropylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (2-isopropylphenyl) ethyl Denhydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (2-isopropylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (2-isopropyl) Phenyl) ethylidenehydrazino] pyrimidine, 4,6-di-n-propyl-2- [1- (2-isopropylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [ 1- (2-isopropylphenyl) ethylidenehydrazino] pyrimidine,
4,6−ジメチル−2−[1−(2−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(2−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(2−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(2−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(2−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(2−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(2−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(2−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(2−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジメチル−2−[1−(2−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(2−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(2−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(2−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(2−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(2−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(2−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(2−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(2−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、 4,6-dimethyl-2- [1- (2-n-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (2-n-butylphenyl) ethylidenehydrazino] Pyrimidine, 4-methyl-6-n-propyl-2- [1- (2-n-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [1- (2-n) -Butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (2-n-butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (2-n-butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (2-n-butylphenyl) ethylidenehydrazino] pyrimidine, , 6-Di-n-propyl-2- [1- (2-n-butylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [1- (2-n- Butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-dimethyl-2- [1- (2-isobutylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (2-isobutylphenyl) ) Ethylidenehydrazino] pyrimidine, 4-methyl-6-n-propyl-2- [1- (2-isobutylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [1- ( 2-isobutylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (2-isobutylphenyl) ethylidenehydrazino] pyrimidine 4-ethyl-6-n-propyl-2- [1- (2-isobutylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (2-isobutylphenyl) ethylidenehydra Dino] pyrimidine, 4,6-di-n-propyl-2- [1- (2-isobutylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [1- (2 -Isobutylphenyl) ethylidenehydrazino] pyrimidine,
4,6−ジメチル−2−[1−(2−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(2−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(2−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(2−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(2−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(2−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(2−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(2−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(2−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジメチル−2−[1−(2−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(2−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(2−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(2−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(2−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(2−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(2−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(2−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(2−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、 4,6-dimethyl-2- [1- (2-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (2-sec-butylphenyl) ethylidenehydrazino] Pyrimidine, 4-methyl-6-n-propyl-2- [1- (2-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [1- (2-sec) -Butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (2-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (2-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (2-sec-butylphenyl) ethyl Nhydrazino] pyrimidine, 4,6-di-n-propyl-2- [1- (2-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [1- (2-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-dimethyl-2- [1- (2-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [ 1- (2-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-propyl-2- [1- (2-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6 -N-butyl-2- [1- (2-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1 (2-tert-Butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (2-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n -Butyl-2- [1- (2-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-di-n-propyl-2- [1- (2-tert-butylphenyl) ethylidenehydrazino] pyrimidine 4-n-propyl-6-n-butyl-2- [1- (2-tert-butylphenyl) ethylidenehydrazino] pyrimidine,
4,6−ジメチル−2−[1−(3−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(3−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(3−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(3−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(3−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(3−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(3−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(3−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(3−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジメチル−2−[1−(3−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(3−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(3−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(3−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(3−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(3−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(3−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(3−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(3−エチルフェニル)エチリデンヒドラジノ]ピリミジン、 4,6-dimethyl-2- [1- (3-methylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (3-methylphenyl) ethylidenehydrazino] pyrimidine, 4- Methyl-6-n-propyl-2- [1- (3-methylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [1- (3-methylphenyl) ethylidenehydrazino] Pyrimidine, 4,6-diethyl-2- [1- (3-methylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (3-methylphenyl) ethylidenehydrazino] Pyrimidine, 4-ethyl-6-n-butyl-2- [1- (3-methylphenyl) ethylidenehydrazino] pyrimidine, 4,6-di-n-propyl-2 [1- (3-Methylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [1- (3-methylphenyl) ethylidenehydrazino] pyrimidine, 4,6-dimethyl- 2- [1- (3-ethylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (3-ethylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n- Propyl-2- [1- (3-ethylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [1- (3-ethylphenyl) ethylidenehydrazino] pyrimidine, 4,6- Diethyl-2- [1- (3-ethylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (3-ethylphenyl) Nyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (3-ethylphenyl) ethylidenehydrazino] pyrimidine, 4,6-di-n-propyl-2- [1- (3-ethylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [1- (3-ethylphenyl) ethylidenehydrazino] pyrimidine,
4,6−ジメチル−2−[1−(3−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(3−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(3−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(3−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(3−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(3−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(3−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(3−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(3−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジメチル−2−[1−(3−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(3−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(3−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(3−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(3−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(3−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(3−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(3−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(3−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、 4,6-dimethyl-2- [1- (3-n-propylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (3-n-propylphenyl) ethylidenehydrazino] Pyrimidine, 4-methyl-6-n-propyl-2- [1- (3-n-propylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [1- (3-n -Propylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (3-n-propylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (3-n-propylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (3-n-propylphenyl) ethylidenehydrazino Pyrimidine, 4,6-di-n-propyl-2- [1- (3-n-propylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [1- (3 -N-propylphenyl) ethylidenehydrazino] pyrimidine, 4,6-dimethyl-2- [1- (3-isopropylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (3 -Isopropylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-propyl-2- [1- (3-isopropylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [ 1- (3-Isopropylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (3-isopropylphenyl) ethyl Denhydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (3-isopropylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (3-isopropyl Phenyl) ethylidenehydrazino] pyrimidine, 4,6-di-n-propyl-2- [1- (3-isopropylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [ 1- (3-isopropylphenyl) ethylidenehydrazino] pyrimidine,
4,6−ジメチル−2−[1−(3−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(3−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(3−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(3−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(3−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(3−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(3−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(3−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(3−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジメチル−2−[1−(3−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(3−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(3−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(3−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(3−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(3−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(3−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(3−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(3−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、 4,6-dimethyl-2- [1- (3-n-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (3-n-butylphenyl) ethylidenehydrazino] Pyrimidine, 4-methyl-6-n-propyl-2- [1- (3-n-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [1- (3-n -Butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (3-n-butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (3-n-butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (3-n-butylphenyl) ethylidenehydrazino] pyrimidine, , 6-Di-n-propyl-2- [1- (3-n-butylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [1- (3-n- Butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-dimethyl-2- [1- (3-isobutylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (3-isobutylphenyl) ) Ethylidenehydrazino] pyrimidine, 4-methyl-6-n-propyl-2- [1- (3-isobutylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [1- ( 3-isobutylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (3-isobutylphenyl) ethylidenehydrazino] pyrimidine 4-ethyl-6-n-propyl-2- [1- (3-isobutylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (3-isobutylphenyl) ethylidenehydra Dino] pyrimidine, 4,6-di-n-propyl-2- [1- (3-isobutylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [1- (3 -Isobutylphenyl) ethylidenehydrazino] pyrimidine,
4,6−ジメチル−2−[1−(3−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(3−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(3−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(3−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(3−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(3−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(3−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(3−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(3−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジメチル−2−[1−(3−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(3−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(3−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(3−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(3−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(3−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(3−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(3−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(3−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、 4,6-dimethyl-2- [1- (3-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (3-sec-butylphenyl) ethylidenehydrazino] Pyrimidine, 4-methyl-6-n-propyl-2- [1- (3-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [1- (3-sec -Butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (3-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (3-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (3-sec-butylphenyl) ethyl Nhydrazino] pyrimidine, 4,6-di-n-propyl-2- [1- (3-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [1- (3-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-dimethyl-2- [1- (3-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [ 1- (3-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-propyl-2- [1- (3-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6 -N-butyl-2- [1- (3-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1 (3-tert-Butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (3-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n -Butyl-2- [1- (3-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-di-n-propyl-2- [1- (3-tert-butylphenyl) ethylidenehydrazino] pyrimidine 4-n-propyl-6-n-butyl-2- [1- (3-tert-butylphenyl) ethylidenehydrazino] pyrimidine,
4,6−ジメチル−2−[1−(4−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(4−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(4−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(4−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(4−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(4−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(4−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(4−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(4−メチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジメチル−2−[1−(4−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(4−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(4−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(4−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(4−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(4−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(4−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(4−エチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(4−エチルフェニル)エチリデンヒドラジノ]ピリミジン、 4,6-dimethyl-2- [1- (4-methylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (4-methylphenyl) ethylidenehydrazino] pyrimidine, 4- Methyl-6-n-propyl-2- [1- (4-methylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [1- (4-methylphenyl) ethylidenehydrazino] Pyrimidine, 4,6-diethyl-2- [1- (4-methylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (4-methylphenyl) ethylidenehydrazino] Pyrimidine, 4-ethyl-6-n-butyl-2- [1- (4-methylphenyl) ethylidenehydrazino] pyrimidine, 4,6-di-n-propyl-2 [1- (4-Methylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [1- (4-methylphenyl) ethylidenehydrazino] pyrimidine, 4,6-dimethyl- 2- [1- (4-ethylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (4-ethylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n- Propyl-2- [1- (4-ethylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [1- (4-ethylphenyl) ethylidenehydrazino] pyrimidine, 4,6- Diethyl-2- [1- (4-ethylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (4-ethylphenyl) Nyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (4-ethylphenyl) ethylidenehydrazino] pyrimidine, 4,6-di-n-propyl-2- [1- (4-ethylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [1- (4-ethylphenyl) ethylidenehydrazino] pyrimidine,
4,6−ジメチル−2−[1−(4−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(4−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(4−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(4−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(4−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(4−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(4−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(4−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(4−n−プロピルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジメチル−2−[1−(4−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(4−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(4−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(4−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(4−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(4−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(4−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(4−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(4−イソプロピルフェニル)エチリデンヒドラジノ]ピリミジン、 4,6-dimethyl-2- [1- (4-n-propylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (4-n-propylphenyl) ethylidenehydrazino] Pyrimidine, 4-methyl-6-n-propyl-2- [1- (4-n-propylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [1- (4-n -Propylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (4-n-propylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (4-n-propylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (4-n-propylphenyl) ethylidenehydrazino Pyrimidine, 4,6-di-n-propyl-2- [1- (4-n-propylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [1- (4 -N-propylphenyl) ethylidenehydrazino] pyrimidine, 4,6-dimethyl-2- [1- (4-isopropylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (4 -Isopropylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-propyl-2- [1- (4-isopropylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [ 1- (4-Isopropylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (4-isopropylphenyl) ethyl Denhydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (4-isopropylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (4-isopropyl) Phenyl) ethylidenehydrazino] pyrimidine, 4,6-di-n-propyl-2- [1- (4-isopropylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [ 1- (4-isopropylphenyl) ethylidenehydrazino] pyrimidine,
4,6−ジメチル−2−[1−(4−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(4−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(4−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(4−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(4−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(4−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(4−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(4−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(4−n−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジメチル−2−[1−(4−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(4−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(4−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(4−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(4−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(4−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(4−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(4−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(4−イソブチルフェニル)エチリデンヒドラジノ]ピリミジン、 4,6-dimethyl-2- [1- (4-n-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (4-n-butylphenyl) ethylidenehydrazino] Pyrimidine, 4-methyl-6-n-propyl-2- [1- (4-n-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [1- (4-n) -Butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (4-n-butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (4-n-butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (4-n-butylphenyl) ethylidenehydrazino] pyrimidine, , 6-Di-n-propyl-2- [1- (4-n-butylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [1- (4-n- Butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-dimethyl-2- [1- (4-isobutylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (4-isobutylphenyl) ) Ethylidenehydrazino] pyrimidine, 4-methyl-6-n-propyl-2- [1- (4-isobutylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [1- ( 4-isobutylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (4-isobutylphenyl) ethylidenehydrazino] pyrimidine 4-ethyl-6-n-propyl-2- [1- (4-isobutylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (4-isobutylphenyl) ethylidenehydra Dino] pyrimidine, 4,6-di-n-propyl-2- [1- (4-isobutylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [1- (4 -Isobutylphenyl) ethylidenehydrazino] pyrimidine,
4,6−ジメチル−2−[1−(4−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(4−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(4−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(4−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(4−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(4−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(4−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(4−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(4−sec−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジメチル−2−[1−(4−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−エチル−2−[1−(4−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−プロピル−2−[1−(4−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−メチル−6−n−ブチル−2−[1−(4−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジエチル−2−[1−(4−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−プロピル−2−[1−(4−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−エチル−6−n−ブチル−2−[1−(4−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4,6−ジ−n−プロピル−2−[1−(4−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン、4−n−プロピル−6−n−ブチル−2−[1−(4−tert−ブチルフェニル)エチリデンヒドラジノ]ピリミジン等が挙げられる。 4,6-dimethyl-2- [1- (4-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [1- (4-sec-butylphenyl) ethylidenehydrazino] Pyrimidine, 4-methyl-6-n-propyl-2- [1- (4-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-butyl-2- [1- (4-sec -Butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1- (4-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (4-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-butyl-2- [1- (4-sec-butylphenyl) ethyl Nhydrazino] pyrimidine, 4,6-di-n-propyl-2- [1- (4-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4-n-propyl-6-n-butyl-2- [1- (4-sec-butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-dimethyl-2- [1- (4-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-ethyl-2- [ 1- (4-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6-n-propyl-2- [1- (4-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4-methyl-6 -N-butyl-2- [1- (4-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-diethyl-2- [1 (4-tert-Butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n-propyl-2- [1- (4-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4-ethyl-6-n -Butyl-2- [1- (4-tert-butylphenyl) ethylidenehydrazino] pyrimidine, 4,6-di-n-propyl-2- [1- (4-tert-butylphenyl) ethylidenehydrazino] pyrimidine 4-n-propyl-6-n-butyl-2- [1- (4-tert-butylphenyl) ethylidenehydrazino] pyrimidine, and the like.
以下、実施例により、本発明をさらに詳細に説明するが、本発明はこれら実施例に限定されない。 EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to these Examples.
[実施例1]
アミノグアニジンの炭酸塩30gおよび水241gを混合した後、内温20℃で濃塩酸70.7gを2時間20分かけて滴下した。内温30℃で30分間攪拌、保持し、アミノグアニジンの塩酸塩を含む水溶液を得た。これに、2’−メチルアセトフェノン29.7gを加え、内温60℃で2時間攪拌、反応させた。反応終了後、内温5℃まで冷却し、同温度にて2時間20分攪拌、保持した。その後、析出固体を濾取した。濾取した固体を乾燥させて、1−(2−メチルフェニル)エチリデンアミノグアニジンの塩酸塩47.8gを得た。含量:95.7重量%、収率:92%(アミノグアニジン基準)。
[Example 1]
After mixing 30 g of aminoguanidine carbonate and 241 g of water, 70.7 g of concentrated hydrochloric acid was added dropwise over 2 hours and 20 minutes at an internal temperature of 20 ° C. The mixture was stirred and held at an internal temperature of 30 ° C. for 30 minutes to obtain an aqueous solution containing aminoguanidine hydrochloride. To this was added 29.7 g of 2′-methylacetophenone, and the mixture was stirred and reacted at an internal temperature of 60 ° C. for 2 hours. After completion of the reaction, the mixture was cooled to an internal temperature of 5 ° C., and stirred and maintained at the same temperature for 2 hours and 20 minutes. Thereafter, the precipitated solid was collected by filtration. The solid collected by filtration was dried to obtain 47.8 g of hydrochloride of 1- (2-methylphenyl) ethylideneaminoguanidine. Content: 95.7% by weight, yield: 92% (based on aminoguanidine).
1−(2−メチルフェニル)エチリデンアミノグアニジンの塩酸塩の元素分析値(C10H15ClN4)
計算値;C=53.0% H=6.7% Cl=15.6% N=24.7%
実測値;C=52.7% H=6.6% Cl=14.7% N=25.0%
Elemental analysis value of hydrochloride of 1- (2-methylphenyl) ethylideneaminoguanidine (C 10 H 15 ClN 4 )
Calculated value: C = 53.0% H = 6.7% Cl = 15.6% N = 24.7%
Actual measurement value: C = 52.7% H = 6.6% Cl = 14.7% N = 25.0%
1−(2−メチルフェニル)エチリデンアミノグアニジンの塩酸塩の1H−NMR(ジメチルスルホキシド−d6,δ/ppm)
2.14(3H,s),2.22(3H,s),2.51(2H,s),7.17〜7.40(4H,m)
1- (2-methylphenyl) ethylidene 1 H-NMR of aminoguanidine hydrochloride (dimethylsulfoxide -d 6, δ / ppm)
2.14 (3H, s), 2.22 (3H, s), 2.51 (2H, s), 7.17-7.40 (4H, m)
前記で得た1−(2−メチルフェニル)エチリデンアミノグアニジンの塩酸塩41.8gおよび水140.8gを混合した後、内温20℃で、ペンタン−2,4−ジオン31.1gを加えた。内温20℃で20重量%炭酸ナトリウム水溶液10.3gを仕込んだ後、内温70℃に昇温した。内温70℃で20重量%炭酸ナトリウム水溶液74.8gを滴下し、反応液のpHを8近傍に調整した。さらに同温度で5時間攪拌、反応させた。なお、この間、反応液のpHが8近傍を保つよう、20重量%炭酸ナトリウム水溶液を適宜追加した。反応終了後、反応液を内温30℃まで冷却し、同温度で2時間攪拌、保持した。析出した固体を濾取した。濾取した固体を乾燥させて、4,6−ジメチル−2−[1−(2−メチルフェニル)エチリデンヒドラジノ]ピリミジン43.7gを得た。収率:97%(1−(2−メチルフェニル)エチリデンアミノグアニジンの塩酸塩基準)。
After mixing 41.8 g of the hydrochloride of 1- (2-methylphenyl) ethylideneaminoguanidine obtained above and 140.8 g of water, 31.1 g of pentane-2,4-dione was added at an internal temperature of 20 ° C. . After charging 10.3 g of a 20 wt% sodium carbonate aqueous solution at an internal temperature of 20 ° C., the internal temperature was raised to 70 ° C. At an internal temperature of 70 ° C., 74.8 g of a 20 wt% sodium carbonate aqueous solution was added dropwise to adjust the pH of the reaction solution to around 8. Further, the mixture was stirred and reacted at the same temperature for 5 hours. During this time, a 20% by weight aqueous sodium carbonate solution was appropriately added so that the pH of the reaction solution was kept at around 8. After completion of the reaction, the reaction solution was cooled to an internal temperature of 30 ° C. and stirred and maintained at the same temperature for 2 hours. The precipitated solid was collected by filtration. The solid collected by filtration was dried to obtain 43.7 g of 4,6-dimethyl-2- [1- (2-methylphenyl) ethylidenehydrazino] pyrimidine. Yield: 97% (based on hydrochloride of 1- (2-methylphenyl) ethylideneaminoguanidine).
Claims (2)
(式中、R1は水素原子または低級アルキル基を表わす。)
で示されるアセトフェノン化合物とを、水中で反応させて、式(2)
(式中、R1は上記と同一の意味を表わす。)
で示されるアミジノヒドラゾン化合物の塩酸塩を得、得られた式(2)で示されるアミジノヒドラゾン化合物の塩酸塩と式(3)
(式中、R2およびR3はそれぞれ同一または相異なって、低級アルキル基を表わす。)で示されるβ−ジケトン化合物とを、水中、pH7〜9の範囲で反応させることを特徴とする式(4)
(式中、R1、R2およびR3は上記と同一の意味を表わす。)
で示されるピリミジン化合物の製造方法。 Aminoguanidine hydrochloride and formula (1)
(In the formula, R 1 represents a hydrogen atom or a lower alkyl group.)
Is reacted with an acetophenone compound represented by the formula (2):
(Wherein R 1 represents the same meaning as described above.)
The hydrochloride of the amidinohydrazone compound represented by formula (2) was obtained, and the hydrochloride of the amidinohydrazone compound represented by formula (2) and formula (3) were obtained.
(Wherein R 2 and R 3 are the same or different and each represents a lower alkyl group) and a β-diketone compound represented by the formula (I) is reacted in water within a pH range of 7-9. (4)
(In the formula, R 1 , R 2 and R 3 have the same meaning as described above.)
The manufacturing method of the pyrimidine compound shown by these.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005231687A JP4760209B2 (en) | 2005-08-10 | 2005-08-10 | Method for producing pyrimidine compound |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005231687A JP4760209B2 (en) | 2005-08-10 | 2005-08-10 | Method for producing pyrimidine compound |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007045739A JP2007045739A (en) | 2007-02-22 |
JP4760209B2 true JP4760209B2 (en) | 2011-08-31 |
Family
ID=37848879
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2005231687A Active JP4760209B2 (en) | 2005-08-10 | 2005-08-10 | Method for producing pyrimidine compound |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP4760209B2 (en) |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS55151570A (en) * | 1979-05-15 | 1980-11-26 | Takeda Chem Ind Ltd | Pyrimidine derivatives, their preparation and antimicrobial for agriculture |
EP0433526A1 (en) * | 1989-12-19 | 1991-06-26 | Richter, Peter, Prof. Dr.sc.nat. | Medicine for the treatment of heart-circulatory illnesses, of arrhythmics in particular |
JPH10114744A (en) * | 1996-08-22 | 1998-05-06 | Takeda Chem Ind Ltd | Aminoguanidinehydrazone derivative, and its production and pharmaceutical preparation |
-
2005
- 2005-08-10 JP JP2005231687A patent/JP4760209B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
JP2007045739A (en) | 2007-02-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2005516064A5 (en) | ||
JP3779616B2 (en) | 4-Hydroxybiphenylhydrazide derivatives | |
JPWO2014103811A1 (en) | Process for producing purified amine compound | |
JP4760209B2 (en) | Method for producing pyrimidine compound | |
JPH02289A (en) | Optically active amine-boron-based compound, asymmetric reducing agent containing the same compound as active ingredient and production of optically active compound using the same agent | |
JP2000007634A5 (en) | ||
CA2448421C (en) | Process for producing quinoline carbaldehyde | |
JPS60202859A (en) | 3-aminoazetidin compound and manufacture | |
JP2005154442A (en) | Method for preparing valsartan and intermediate thereof | |
US3244750A (en) | Nu, nu'-disubstituted-aliphatic-bis-aminomethyl-cyclohexane derivatives | |
JP3241760B2 (en) | Cyclohexanone derivative | |
CA2507691A1 (en) | Method for producing salts of tolperisone | |
WO2010100990A1 (en) | Process for the production of nucleophilic adducts by grignard reaction, and nucleophilic addition reactant | |
KR100662110B1 (en) | Preparation of tetrazol derivatives | |
JP3950422B2 (en) | Azadirs Alder Reaction Method | |
JPWO2006001537A1 (en) | Method for producing hydrazone compound | |
JPH05508633A (en) | Intermediates used in the preparation of deferoxamine | |
JP3472763B2 (en) | Complexes for synthesis of dialkylamino alcohols | |
JP2016108332A (en) | Method for producing amino compound | |
JPH02164A (en) | Preparation of retinal | |
JP4840716B2 (en) | Method for producing 4 (5) -cyanoimidazole derivative | |
US20080269516A1 (en) | Process for Preparing the Intermediate Compounds for Pparalpha Ligands | |
US8563749B2 (en) | Process for preparing substituted 1,3-dihydro-2H-indol-2-ones | |
JPS58121284A (en) | Preparation of amino peroxide | |
JP2002326978A (en) | Method for producing 4-aminocyclohexyl acetic acid or its ester |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A712 Effective date: 20071126 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20071126 |
|
RD05 | Notification of revocation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7425 Effective date: 20080131 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080422 |
|
RD05 | Notification of revocation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7425 Effective date: 20080515 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20101215 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110111 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110207 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20110510 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20110523 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140617 Year of fee payment: 3 |
|
R151 | Written notification of patent or utility model registration |
Ref document number: 4760209 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R151 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140617 Year of fee payment: 3 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |