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A New Approach to the Synthesis of Hydrogenated Pyrimidine-2-imines
1  Department of Organic Chemistry, State Academy of Fine Chemical Technology, Vernadsky Avenue 86, Moscow 117571, Russia

Abstract: A new convenient method for the synthesis of hydrogenated 2-cyaniminopyrimidines has been developed. This method is based on preparation of a-tosyl substituted N-cyanoguanidines 11 followed by reaction with enolates of a-functionally substituted ketones to give 5-functionalized 2-cyanimino-4-hydroxypyrimidines 12, 13, 15, 16. All the obtained hydroxypyrimidines are readily converted into the corresponding 5-functionalized 2-cyanimino-1,2,3,4-tetrahydrohydropyrimidines 17-20 by heating in the presence of acids. Treatment of 5-acetyl-4-hydroxypyrimidines 12 with aq. KOH gives 4-hydroxypyrimidines 21 in result of removing the acetyl group
Keywords: N-cyanoguanidine, N-cyano-N'-(1-tosyl-1-alkyl)guanidines, a-functionally substituted ketones, 2-cyanimino-4-hydroxyhexahydropyrimidines, 2-cyanimino-1,2,3,4-tetrahydropyrimidines