Reactions of isomeric 6-methyl-2-methylthio-4-cyanomethoxypyrimidine and 6-methyl-2-methylthio-3-cyanomethylpyrimidinone-4 with N-nucleophiles

Abstract

It was found that 6-methyl-2-methylthio-4-cyanomethoxypyrimidine (O-isomer) reacted via the cyano group with ammonia and hydroxylamine to give an amidine and an amidoxime respectively. The O-isomer did not react with either primary or secondary amines under similar conditions, but nucleophilic substitution at position 2 of the O-isomer was effected by converting the 2-methylthio group into a 2-methylsulfonyl. 6-Methyl-2-methylthio-3-cyanomethylpyrimidinone-4 (N₃-isomer) formed imidazo[1,2-a]pyrimidinones-5 with ammonia and primary amines, 2-amino-6-methyl-3-cyanomethylpyrimidinones-4 with secondary amines and either an amidoxime or an imidazo[1,2-a]pyrimidinone-5 with hydroxylamine, depending on the reaction temperature.

How to Cite
Syadyaryavichyute, V.; Vaínilavichyus, P. Chem. Heterocycl. Compd. 1996, 32, 605. [Khim. Geterotsikl. Soedin. 1996, 703.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01164794