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Report | Regular issue | Vol 23, No. 11, 1985, pp.2819-2828
Published online, 1st January, 1970
DOI: 10.3987/R-1985-11-2819
Syntheses and Transformations of 4-Amino-2-methylthio- and 4-Amino-2-methoxypyrimidine-5-carboxamide Oximes

Branko Stanovnik,* Uros Urleb, and Miha Tisler

*Department of Chemistry, E. Kardelj University, Murnikova 6, 61000 Ljubljana, Slovenia


4-Amino-5-cyano-2-methylthio- (1) and 4-amino-5-cyano-2-methoxypyrimidine (13) were transformed with hydroxylamine into the corresponding pyrimidine-5-carboxamide oximes (2 and 14). Acylation and carbethoxylation under mild conditions produced O-substituted carboxamide oximes (3, 7, 9, 15, 18, and 19), while under more vigorous conditions cyclization occurred producing 5-(1,2,4-oxadiazolyl)-pyrimidines (4, 6, 8, and 16).