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Synthesis and reactions of n ‐methyl‐4‐(methylthio)thieno[2,3‐ d ]‐pyrimidinium salts
Author(s) -
Maruoka Hiroshi,
Okabe Fumi,
Yamagata Kenji
Publication year - 2008
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.5570450543
Subject(s) - chemistry , sodium methoxide , malononitrile , methanethiol , methylene , ethyl cyanoacetate , medicinal chemistry , nucleophile , sodium , sodium salt , stereochemistry , organic chemistry , methanol , sulfur , catalysis , inorganic chemistry
Two methods for the preparation of N ‐methyl‐4‐(methylthio)thieno[2,3‐ d ]pyrimidinium salts 6a,b and 13a,b are described. Treatment of 6a,b and/or 13a,b with active methylene compounds such as malononitrile and ethyl cyanoacetate in the presence of sodium methoxide caused nucleophilic addition followed by elimination of methanethiol, giving the corresponding N ‐methyl‐4‐ylidenethieno[2,3‐ d ]‐pyrimidines 7a,b, 8a,b, 14a,b and 15a,b .