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Pyrimidines. 65 . Synthesis of 6‐substituted thieno[2,3‐ d ]pyrimidine‐2,4(1 H ,3 H )‐diones
Author(s) -
Hirota Kosaku,
Shirahashi Mitsuomi,
Senda Shigeo,
Yogo Motoi
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270345
Subject(s) - chemistry , pyrimidine , nitration , halogenation , medicinal chemistry , electrophile , electrophilic substitution , condensation , base (topology) , stereochemistry , organic chemistry , catalysis , mathematical analysis , physics , mathematics , thermodynamics
Several 6‐substituted thieno[2,3‐ d ]pyrimidine‐2,4(1 H ,3 H )‐dione derivatives were synthesized. 6‐Ethoxycarbonyl derivatives 3 and 7 were prepared by treatment of 6‐chloro‐5‐formyluracil 1 and 6‐chloro‐5‐cyanouracil 6 with ethyl 2‐mercaptoacetate in the presence of a base. Electrophilic substitution reactions (Vilsmeier‐Haack reaction, bromination, and nitration) of 5,6‐unsubstituted thieno[2,3‐ d ]pyrimidine 9 , prepared by condensation of 6‐mercaptouracil 8 with chloroacetaldehyde, afforded the corresponding 6‐formyl‐, 6‐bromo‐, and 6‐nitrothieno[2,3‐ d ]pyrimidines 10, 15 and 16 , respectively.