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DD245666A1 - PROCESS FOR PREPARING 4-AMINO-SUBSTITUTED THIENO 2,3-D-PYRIMIDIN-2-YLESSED ACID ESTERS - Google Patents

PROCESS FOR PREPARING 4-AMINO-SUBSTITUTED THIENO 2,3-D-PYRIMIDIN-2-YLESSED ACID ESTERS Download PDF

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Publication number
DD245666A1
DD245666A1 DD28082185A DD28082185A DD245666A1 DD 245666 A1 DD245666 A1 DD 245666A1 DD 28082185 A DD28082185 A DD 28082185A DD 28082185 A DD28082185 A DD 28082185A DD 245666 A1 DD245666 A1 DD 245666A1
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German Democratic Republic
Prior art keywords
pyrimidin
general formula
alkyl
amino
substituted thieno
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DD28082185A
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German (de)
Inventor
Ralf Boehm
Gunter Laban
Dieter Lohmann
Reinhard Pech
Thomas Eisenaecher
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Univ Halle Wittenberg
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Priority to DD28082185A priority Critical patent/DD245666A1/en
Publication of DD245666A1 publication Critical patent/DD245666A1/en

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Abstract

Die Erfindung betrifft ein Verfahren zur Herstellung von 4-aminosubstituierten Thieno(2,3-d)pyrimidin-2-ylessigsaeureestern der allgemeinen Formel I, worinR1, R2 H, Alkyl, Polymethylen, PhenylR3 AlkylR4 H, AlkylenR5 Aryl, Alkylenbedeuten.Diese Verbindungen stellen potentielle Pharmaka dar und sind gleichzeitig Zwischenprodukte der pharmazeutischen Industrie. Ziel der Erfindung ist es, ausgehend von 3,4-Dihydro-4-oxothieno(2,3-d)pyrimidin-2-ylessigsaeureestern der allgemeinen Formel II, worinR1, R2 H, Alkyl, Polymethylen, PhenylR3 Alkylbedeuten,4-aminosubstituierte Thieno(2,3-d)pyrimidin-2-ylessigsaeureester darzustellen. Die Synthese der Verbindungen der allgemeinen Formel I erfolgt durch Umsetzung der 3,4-Dihydro-4-oxothieno(2,3-d)pyrimidin-2-ylessigsaeureester der allgemeinen Formel II mit Phosphoroxidchlorid, wobei die dabei anfallenden 4-Chlorthieno(2,3-d)-pyrimidin-2-ylessigsaeureesterder allgemeinen Formel III anschliessend mit primaeren oder secundaeren Aminen in einem protischen organischen Loesungsmittel in der Siedehitze zu den Endprodukten umgesetzt werden.The invention relates to a process for the preparation of 4-amino-substituted thieno (2,3-d) pyrimidin-2-ylessigsaeureestern of the general formula I, whereinR1, R2 is H, alkyl, polymethylene, phenylR3 alkyl R4 H, alkylenesyl R5 aryl, alkylene. These compounds provide are potential drugs and are also intermediates of the pharmaceutical industry. The aim of the invention is, starting from 3,4-dihydro-4-oxothieno (2,3-d) pyrimidin-2-ylessigsaeureestern of the general formula II, whereinR1, R2 is H, alkyl, polymethylene, phenylR3 alkyl, 4-amino-substituted thieno (2,3-d) pyrimidin-2-ylessigsaeureester represent. The synthesis of the compounds of general formula I is carried out by reacting the 3,4-dihydro-4-oxothieno (2,3-d) pyrimidin-2-ylessigsaeureester the general formula II with phosphorus oxychloride, wherein the resulting 4-Chlorthieno (2, 3-d) -pyrimidin-2-ylessigsaeureesterder general formula III are then reacted with primary or secondary amines in a protic organic solvent in the boiling heat to the final products.

Description

Anwendungsgebiet der ErfindungField of application of the invention

Die Erfindung betrifft ein Verfahren zur Synthese von 4-amino-substituierten Thieno[2,3-d]pyrimidin-2-ylessigsäureestern der allgemeinen Formel I, worin R1, R2 = H, Alkyl, Polymethylen, PhenylThe invention relates to a method for the synthesis of 4-amino-substituted thieno [2,3-d] pyrimidin-2-ylessigsäureestern the general formula I, wherein R 1 , R 2 = H, alkyl, polymethylene, phenyl

R3 = AlkylR 3 = alkyl

R4 = H,AlkylenR 4 = H, alkylene

R5 = Aryl,AlkylenR 5 = aryl, alkylene

bedeutenmean

Die Verbindungen stellen potentielle Pharmaka und gleichzeitig Zwischenprodukte der pharmazeutischen Industrie dar. The compounds are potential drugs and also intermediates of the pharmaceutical industry.

Charakteristik der bekannten technischen LösungenCharacteristic of the known technical solutions

Verbindungen der allgemeinen Formel I werden bisher weder in der Patent- noch in der Fachliteratur beschrieben. Damit wird erstmals am Thieno[2,3-d]pyrimidin sowohl ein Amino- als auch ein Essigsäureestersubstituent gebunden sein, (vergleiche: 4-aminosubstituierte Thieno/2,3-d/pyrimidin-2 tow. -6-ylcarbonsäureester, WP C 07 D 272506/0 und WP C D 272507/7)Compounds of the general formula I are so far described neither in the patent nor in the specialist literature. Thus, both an amino and an acetic acid ester substituent will be bound to thieno [2,3-d] pyrimidine for the first time, (compare: 4-amino-substituted thieno / 2,3-d / pyrimidine-2-bis-6-ylcarboxylic acid ester, WP C 07 D 272506/0 and WP CD 272507/7)

Ziel der ErfindungObject of the invention

Ziel der Erfindung ist eine einfache und schnelle Herstellungsmethode für bisher nicht zugängliche 4-aminosubstituierte Thieno-[2,3-d]pyrimidin-2-ylessigsäureester der allgemeinen Formel I mit gut zugänglichen Ausgangsprodukten, um die Palette potentieller Pharmaka bzw. interessanter Zwischenprodukte zu erweitern.The aim of the invention is a simple and rapid production method for hitherto inaccessible 4-amino-substituted thieno [2,3-d] pyrimidin-2-ylessigsäureester the general formula I with readily available starting materials to expand the range of potential drugs or interesting intermediates ,

Darstellung des Wesens der ErfindungPresentation of the essence of the invention

Aufgabe der Erfindung ist ein Verfahren zur Synthese von 4-amino-substituierten Thieno[2,3-d]pyrimidin-2-ylessigsäureestem der allgemeinen Formel I, worin R1, R2 = H, Alkyl, Polymethylen, PhenylThe object of the invention is a process for the synthesis of 4-amino-substituted thieno [2,3-d] pyrimidin-2-ylessigsäureestem of the general formula I, wherein R 1 , R 2 = H, alkyl, polymethylene, phenyl

R3 = AlkylR 3 = alkyl

R< =H,AlkylenR <= H, alkylene

R5 = Aryl,AlkylenR 5 = aryl, alkylene

bedeuten.mean.

Erfindungsgemäß wird die Aufgabe dadurch gelöst, daß 3,4-Dihydro-4-oxothieno[2,3-d]pyrimidin-2-ylessigsäureester der allgemeinen Formel II, worin R1,R2 = H,Alkyl, Polymethylen, PhenylAccording to the invention the object is achieved in that 3,4-dihydro-4-oxothieno [2,3-d] pyrimidin-2-ylessigsäureester of the general formula II, wherein R 1 , R 2 = H, alkyl, polymethylene, phenyl

R3 = AlkylR 3 = alkyl

bedeuten,mean,

mit Phosphoroxidchlorid in die 4-Chlorthieno[2,3-d]pyrimidin-2-ylessigsäureester der allgemeinen Formel III, worin R1, R2 = H, Alkyl, Polymethylen, Phenylwith phosphorus oxychloride into the 4-chlorothieno [2,3-d] pyrimidin-2-ylacetic acid esters of general formula III, wherein R 1 , R 2 = H, alkyl, polymethylene, phenyl

R3 = AlkylR 3 = alkyl

bedeuten,mean,

überführt werden und diese anschließend mit einem primären oder sekundären Amin in einem protischen organischen Lösungsmittel in der Siedehitze zu den 4-aminosubstituierten Thieno-[2,3-d]pyrimidin-2-ylessigsäureestem der allgemeinen Formel I, worin R1, R2, R3, R4 und R5 obige Bedeutung besitzen, umgesetzt werden. Die Aufarbeitung der Zwischen- und Endprodukte erfolgt in an sich bekannter Weise.and then reacting these with a primary or secondary amine in a protic organic solvent at boiling temperature to give the 4-amino-substituted thieno [2,3-d] pyrimidin-2-yl-acid esters of general formula I wherein R 1 , R 2 , R 3 , R 4 and R 5 have the above meaning, be implemented. The work-up of the intermediate and end products takes place in a manner known per se.

Ausführungsbeispieleembodiments

Πιο FrfinHiinn or\ll narhctohonH an ·τ\Λΐοΐ Poicnialan orläntor+u/orHon1 Frιο FrfinHiinn or \ ll narhctohonH an · τ \ Λΐοΐ Poicnialan orlander + u / orHon 1

Beispiel 1example 1

4-Chlorthieno[2,3-d]pyrimidin-2-ylessigsäureester (Formel III) Allgemeine Vorschrift:4-Chlorothieno [2,3-d] pyrimidin-2-ylacetic acid ester (Formula III) General rule:

0,01 mol der 3,4-Dihydro-4-oxothieno[2,3-d]pyrimidin-2-yl-essigsäureester werden mit 2,3ml Ν,Ν-Dimethylanilin und 10ml Phosphoroxidchlorid 4,5 Stunden unter Rückfluß erhitzt. Nach Beendigung der Umsetzung wird nicht umgesetztes POCI3 im Vakuum abdestilliert und der Rückstand vorsichtig auf Eis gegossen. Nach Neutralisation mit Sodalösung saugt man ab und extrahiert erschöpfend mit heißem Benzin. Die Benzinphase wird filtriert und auf Vs des ursprünglichen Volumens eingeengt. Die dabei anfallenden Produkte sind dürinschichtchromatographisch einheitlich. Nach dieser allgemeinen Vorschrift werden die in Tabelle I zusammengefaßten Verbindungen hergestellt:0.01 mol of the 3,4-dihydro-4-oxothieno [2,3-d] pyrimidin-2-yl-acetic acid ester are refluxed with 2.3 ml of Ν, Ν-dimethylaniline and 10 ml of phosphorus oxychloride for 4.5 hours. After completion of the reaction, unreacted POCl 3 is distilled off in vacuo and the residue carefully poured onto ice. After neutralization with sodium carbonate solution is filtered off with suction and extracted exhaustively with hot gasoline. The petrol phase is filtered and concentrated to Vs of the original volume. The resulting products are dininschichtchromatographie uniform. Following this general procedure, the compounds summarized in Table I are prepared:

Tabelle ITable I R2 R 2 R3 R 3 SummenformelMolecular formula Molmassemolar mass Ausbeute (%)Yield (%) Schmelzpunkt (0C)Melting point ( 0 C) R1 R 1 CH3 CH 3 C2H5 C 2 H 5 C12H13CIN2O2SC 12 H 13 CIN 2 O 2 S 284,8284.8 4444 57-6157-61 CH3 CH 3 CH3 CH 3 C13H13CIN2O2SC 13 H 13 CIN 2 O 2 S 296,8296.8 4141 92-9492-94 -(CH2I4-- (CH 2 I 4 - C2H5 C 2 H 5 C14H15CIN2O2SC 14 H 15 CIN 2 O 2 S 310,8310.8 6262 57-6057-60 -(CH2J4-- (CH 2 J 4 - HH CH3 CH 3 C15H11CIN2O2SC 15 H 11 CIN 2 O 2 S 318,8318.8 1515 12V12512V125 C6H5 C 6 H 5 HH C2H5 C 2 H 5 C16H13CIN2O2SC 16 H 13 CIN 2 O 2 S 332,8332.8 5656 78-8178-81 C6H5 C 6 H 5

Beispiel 2Example 2

4-Aminothieno[2,3-d]pyrimidin-2-ylessigsäureester (Formel I)4-aminothieno [2,3-d] pyrimidin-2-ylacetic acid ester (formula I)

Allgemeine Vorschrift:General rule:

0,005mol 4-Chiorthieno[2,3-d]pyrimidin-2-ylessigsäureester werden mit 0,011 mol primärem aromatischem und sekundärem aliphatischem Amin in 8ml Ethanol unter Rückfluß gekocht. Nach dünnschichtchromatographischer Bestimmung des Reaktionsendes kristallisieren beim Abkühlen die Endprodukte aus. Nach Absaugen werden die Kristalle mit warmem Wasser gewaschen und aus dem R3 entsprechenden (Allgemeine Formel I) Alkohol umkristallisiert.0.005 moles of 4-chiorthieno [2,3-d] pyrimidin-2-ylacetic acid ester are refluxed with 0.011 moles of primary aromatic and secondary aliphatic amine in 8 ml of ethanol. After determination of the end of the reaction by thin-layer chromatography, the end products crystallize on cooling. After aspiration, the crystals are washed with warm water and recrystallized from the corresponding R 3 (general formula I) alcohol.

In den nachfolgenden Tabellen II, IM und IV werden die nach dieser allgemeinen Vorschrift hergestellten Verbindungen zusammengefaßt:Tables II, IM and IV below summarize the compounds prepared according to this general rule:

Tabelle Il 4-Arylarnino-5,6-tetramethylenthieno[2,3-d]pyrimidin-2-ylessigsäureesterTable II 4-Arylarnino-5,6-tetramethylenethieno [2,3-d] pyrimidin-2-ylacetic acid ester

R3 R 3

Summenformel Molmasse Ausbeute (%) Schmelzpunkt (0°C)Molecular Formula Molecular Weight Yield (%) Melting Point (0 ° C)

HH C2H5 C 2 H 5 C20H21N3O2SC 20 H 21 N 3 O 2 S 367,4367.4 7171 110-112110-112 o-CH3 o-CH 3 C2H5 C 2 H 5 C21H23N3O2SC 21 H 23 N 3 O 2 S 381,5381.5 2121 129-133129-133 m-CH3 m-CH 3 C2H5 C 2 H 5 C21H23N3O2SC 21 H 23 N 3 O 2 S 381,5381.5 4646 131-133131-133 P-CH3 P-CH 3 C2H5 C 2 H 5 C21H23N3O2SC 21 H 23 N 3 O 2 S 318,5318.5 5252 135-137135-137 p-Fp-F C2H5 C 2 H 5 C20H20FN3O2SC 20 H 20 FN 3 O 2 S 383,5383.5 2626 125-127125-127 m-CI, p-Fm-CI, p-F C2H5 C 2 H 5 C20H19CIFN3O2SC 20 H 19 CIFN 3 O 2 S 419,9419.9 5050 132-135132-135 o-CIo-CI C2H5 C 2 H 5 C20H20CIN3O2SC 20 H 20 CIN 3 O 2 S 401,9401.9 3535 148-151148-151 m-CIm-Cl C2H5 C 2 H 5 C20H20CIN3O2SC 20 H 20 CIN 3 O 2 S 401,9401.9 4848 137-139137-139 p-CIp-Cl C2H5 C 2 H 5 C20H20CIN3O2SC 20 H 20 CIN 3 O 2 S 401,9401.9 3939 142-144142-144 o-OCH3 o-OCH 3 C2H5 C 2 H 5 C21H23N3O3SC 21 H 23 N 3 O 3 S 397,5397.5 5555 154-156154-156 m-0CH3 m-0CH 3 C2H5 C 2 H 5 C21H23N3O3SC 21 H 23 N 3 O 3 S 397,5397.5 6464 119-121119-121 P-OCH3 P-OCH 3 C2H5 C 2 H 5 C21H23N3O3SC 21 H 23 N 3 O 3 S 397,5397.5 5353 147-149147-149 P-CO2C2H6 P-CO 2 C 2 H 6 C2H5 C 2 H 5 C23H25N3O4SC 23 H 25 N 3 O 4 S 439,5439.5 5555 147-150147-150 o-CO2Ho-CO 2 H C2H5 C 2 H 5 C21H21N3O4SC 21 H 21 N 3 O 4 S 411,5411.5 2929 208-210208-210 HH CH3 CH 3 C19H19N3O2SC 19 H 19 N 3 O 2 S 353,4353.4 55 107-110107-110 m-CI, p-Fm-CI, p-F CH3 CH 3 C19H17CIFN3O2SC 19 H 17 CIFN 3 O 2 S 405,9405.9 9191 178-182178-182 m-CIm-Cl CH3 CH 3 C19H13CIN3O2SC 19 H 13 CIN 3 O 2 S 387,9387.9 3636 138-141138-141

Tabelle III 4-Arylamino-5,6-dimethylthieno[2,3-d]pyrimidin-2-ylessigsäureethylesterTable III 4-Arylamino-5,6-dimethylthieno [2,3-d] pyrimidin-2-ylacetic acid ethyl ester

KgH6 KgH 6

R6 R 6 SummenformelMolecular formula Molmassemolar mass Ausbeute (%)Yield (%) Schmelzpunkt (0C)Melting point ( 0 C) HH C18H19N3O2SC 18 H 19 N 3 S 2 O 341,4341.4 3737 145-147145-147 o-CH3 o-CH 3 C18H21N3O2SC 18 H 21 N 3 O 2 S 355,5355.5 99 148-155148-155 m-CHgm-CHg C19H21N3O2SC 19 H 21 N 3 O 2 S 355,5355.5 3535 119-121119-121 P-CH3 P-CH 3 C19H21N3O2SC 19 H 21 N 3 O 2 S 355,5355.5 3737 113-117113-117 p-Fp-F C18H18FN3O2SC 18 H 18 FN 3 O 2 S 359,4359.4 6363 129-132129-132 m-CI, p-Fm-CI, p-F C18H17CIFN3O2SC 18 H 17 CIFN 3 O 2 S 393,9,393.9, 3939 120-122120-122 m-CIm-Cl C18H18CIN3O2SC 18 H 18 CIN 3 O 2 S 375,8375.8 1919 149-151149-151 p-CIp-Cl C18H18CIN3O2SC 18 H 18 CIN 3 O 2 S 395,8395.8 1313 150-152150-152 0-OCH3 0-OCH 3 C19H21N3SO3SC 19 H 21 N 3 SO 3 S 371,5371.5 4646 150-153150-153 m-0CH3 m-0CH 3 C19H21N3SO3SC 19 H 21 N 3 SO 3 S 371,5371.5 2222 127-129127-129 P-OCH3 P-OCH 3 C19H21N3SO3SC 19 H 21 N 3 SO 3 S 371,5371.5 55 111-113111-113 P-CO2C2H5 P-CO 2 C 2 H 5 C21H23N3O4SC 21 H 23 N 3 O 4 S 413,5413.5 4949 138-140138-140 0-CO2H0-CO 2 H C19H19N3O4SC 19 H 19 N 3 O 4 S 385,4385.4 55 237-240237-240

Tabelle IV 4-Arylamino-5-phenylthieno[2,3-d]pyrimidin-2-ylessigsäureesterTable IV 4-Arylamino-5-phenylthieno [2,3-d] pyrimidin-2-ylacetic acid ester

Summenformel Molmasse Ausbeute (%) Schmelzpunkt (0C)Molecular Formula Molecular Weight Yield (%) Melting Point ( 0 C)

HH CH3 CH 3 C21H17N3O2SC 21 H 17 N 3 O 2 S 387,4387.4 HH C2H5 C 2 H 5 C22H19N3O2SC 22 H 19 N 3 O 2 S 375,4375.4 0-CH3 0-CH 3 C2H5 C 2 H 5 C23H21N3O2SC 23 H 21 N 3 O 2 S 403,5403.5 m-CH3 m-CH 3 C2H5 C 2 H 5 C23H21N3O2SC 23 H 21 N 3 O 2 S 403,5403.5 P-CH3 P-CH 3 C2H5 C 2 H 5 C23H21N3O2SC 23 H 21 N 3 O 2 S 403,5403.5 p-Fp-F C2H5 C 2 H 5 C22H18FN3O2SC 22 H 18 FN 3 O 2 S 407,5407.5 m-CI, p-Fm-CI, p-F C2H5 C 2 H 5 C22H17CIFN3O2SC 22 H 17 CIFN 3 O 2 S 441,9441.9 m-CIm-Cl C2H5 C 2 H 5 C22H18CIN3O2SC 22 H 18 CIN 3 O 2 S 423,9423.9 p-CIp-Cl C2H5 C 2 H 5 C22H18CIN3O2SC 22 H 18 CIN 3 O 2 S 423,9423.9 0-OCH3 0-OCH 3 C2H5 C 2 H 5 C23H21N3O3SC 23 H 21 N 3 O 3 S 419,5419.5 P-OCH3 P-OCH 3 C2H5 C 2 H 5 C23H21N3O3SC 23 H 21 N 3 O 3 S 419,5419.5 P-CO2C2H5 P-CO 2 C 2 H 5 C2H5 C 2 H 5 C25H23N3O4SC 25 H 23 N 3 O 4 S 461,5461.5 Q-CO2HQ-CO 2 H C2H5 C 2 H 5 C32H19N3O4SC 32 H 19 N 3 O 4 S 433,5433.5

6 746 74

54 41 42 43 25 13 13 47 2254 41 42 43 25 13 13 47 22

94-96 107-109 158-16194-96 107-109 158-161

71-73 114-118 100-102 118-12071-73 114-118 100-102 118-120

94-9694-96

88-90 132-135 125-127 115-117 271-27488-90 132-135 125-127 115-117 271-274

In analoger Weise wird dargestellt:In an analogous way is shown:

4-Morpholino-5,6-tetramethylenthieno[2,3-d]pyrimidin-2-ylessigsäureethylester, Ci8H23N3O3S, (361,5) Schmelzpunkt: 112-114°C, Ausbeute: 18%4-Morpholino-5,6-tetramethylenethieno [2,3-d] pyrimidin-2-ylacetic acid ethyl ester, Ci 8 H 23 N 3 O 3 S, (361.5) Melting point: 112-114 ° C, Yield: 18%

lt l t

-.1 -,2-.1 -, 2

' X j j^O-Lj* 1^i'X jj ^ O-Lj * 1 ^ i

I?-I? -

ox'insl X"ox'insl X "

O1 -,2 _ „ O 1 - 2 _ "

j-.-op23 = H, AlIrj -.- o p2 3 = H, AlIr

ρ"ι α -,-!-rlρ "ι α -, -! - rl

iJ -1JiJ - 1 y

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung von 4-aminosubstituierten Thieno[2,3-d]-pyrimidin-2-ylessigsäureestern der allgemeinen Formel I, worin R1, R2 = H,Alkyl, Polymethylen, PhenylA process for the preparation of 4-amino-substituted thieno [2,3-d] pyrimidin-2-yl-acid esters of general formula I, wherein R 1 , R 2 = H, alkyl, polymethylene, phenyl R3 = AlkylR 3 = alkyl R4 = H.AIkylenR 4 = H.Alkylen rs =Aryl,Alkylenrs = aryl, alkylene bedeuten,mean, gekennzeichnet dadurch, daß 3,4-Dihydro-4-oxothieno[2,3-d]-pyrimidin-2-ylessigsäureester der allgemeinen Formel II, worin R1, R2 = H, Alkyl, Polymethylen, Phenylcharacterized in that 3,4-dihydro-4-oxothieno [2,3-d] pyrimidin-2-ylacetic acid ester of general formula II, wherein R 1 , R 2 = H, alkyl, polymethylene, phenyl R3 = AlkylR 3 = alkyl bedeuten, mit Phosphoroxidchlorid in die 4-Chlorthieno[2,3-d]pyrimidin-2-ylessigsäureester der allgemeinen Formel III, worin R1, R2 und R3 obige Bedeutung besitzen, überführt und diese anschließend mit einem primären oder sekundären Amin in einem protischen organischen Lösungsmittel in der Siedehitze zu den Endprodukten der allgemeinen Formel I umgesetzt werden. Hierzu eine Seite Formeln.mean, with phosphorus oxychloride in the 4-Chlorthieno [2,3-d] pyrimidin-2-ylessigsäureester of the general formula III, wherein R 1 , R 2 and R 3 have the above meanings, and then with a primary or secondary amine in a protic organic solvent in the boiling heat to the final products of general formula I are reacted. For this a page formulas.
DD28082185A 1985-09-20 1985-09-20 PROCESS FOR PREPARING 4-AMINO-SUBSTITUTED THIENO 2,3-D-PYRIMIDIN-2-YLESSED ACID ESTERS DD245666A1 (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999028325A1 (en) * 1997-11-28 1999-06-10 Merck Patent Gmbh Thienopyrimidines
WO2009104026A1 (en) * 2008-02-19 2009-08-27 Vichem Chemie Kutató Kft Tricyclic benzo[4,5]thieno-[2,3-d]pyrimidine-4-yl-amin derivatives, their salts, process for producing the compounds and their pharmaceutical use
AU2013202368B2 (en) * 2012-01-25 2016-06-16 Proteostasis Therapeutics, Inc. Proteasome activity modulating compounds
US9981981B2 (en) 2010-07-23 2018-05-29 President And Fellows Of Harvard College Tricyclic proteasome activity enhancing compounds

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999028325A1 (en) * 1997-11-28 1999-06-10 Merck Patent Gmbh Thienopyrimidines
AU742433B2 (en) * 1997-11-28 2002-01-03 Merck Patent Gmbh Thienopyrimidines
WO2009104026A1 (en) * 2008-02-19 2009-08-27 Vichem Chemie Kutató Kft Tricyclic benzo[4,5]thieno-[2,3-d]pyrimidine-4-yl-amin derivatives, their salts, process for producing the compounds and their pharmaceutical use
US8802849B2 (en) 2008-02-19 2014-08-12 Vichem Chemie Kutató Kft. Tricyclic benzo[4,5]thieno-[2,3-d]pyrimidine-4-yl-amin derivatives, their salts, process for producing the compounds and their pharmaceutical use
US9981981B2 (en) 2010-07-23 2018-05-29 President And Fellows Of Harvard College Tricyclic proteasome activity enhancing compounds
AU2013202368B2 (en) * 2012-01-25 2016-06-16 Proteostasis Therapeutics, Inc. Proteasome activity modulating compounds
US9399647B2 (en) 2012-01-25 2016-07-26 Proteostasis Therapeutics, Inc. Proteasome activity modulating compounds

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