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Synthesis of thieno[2,3‐ d ]pyrimidines from 4,6‐dichloropyrimidine‐5‐carbaldehydes
Author(s) -
Clark J.,
Shahhet M. S.,
Korakas D.,
Varvounis G.
Publication year - 1993
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.5570300439
Subject(s) - chemistry , nitration , hydrolysis , intramolecular force , nitro , medicinal chemistry , base (topology) , organic chemistry , mathematical analysis , alkyl , mathematics
Several thieno[2,3‐ d ]pyrimidines have been prepared by intramolecular cyclisation of 6‐(substituted methylthio)‐5‐pyrimidinecarbaldehyde and carbonitrile intermediates derived from 6‐chloropyrimidine‐5‐carbaldehydes and 5‐carbonitriles and methyl thioglycolate or 5‐formylpyrimidine‐4‐(3 H )‐thiones and appropriate α‐halogeno compounds. Thienopyrimidines 18 and 5c were nitrated to the corresponding nitro compounds 23 and 24 . Hydrolysis at position 4 of compound 18 also occurred during nitration. The ester 5g was hydrolysed in base to the acid 25 .