An N-nitroso group was used to activate chloropyrimidines toward nucleophilic substitution by amines. This permitted a simple, one-pot, high-yielding synthesis of pyrimidine-4,6-and -2,4-diamines.
Two methods of synthesis of aryl (pyrimidin-3-yl)methyl ureas were investigated. One of them involved reaction sequence starting with (pyrimidin-3-yl)acetohydrazides to give the corresponding azides, which reacted with aryl amines to form aryl (pyrimidin-3-yl)methyl ureas. The second one was based on a one-pot reaction of (pyrimidin-3-yl)acetic acids with diphenyl phosphoryl azide followed by reaction with aryl amines. Also, some new aryl and (pyrimidin-3-yl) moiety bearing hydrazones and semicarbazones were synthesized.
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