4-Amino-5-(arylaminomethyl)-2-(methylthio)furo[2,3-d]pyrimidines via Mitsunobu Reaction of 4-Amino-5-(hydroxymethyl)-2-(methylthio)furo[2,3-d]pyrimidine with N-Mesyl- and N-Nosylarylamines

Abstract

An efficient method for the synthesis of 4-amino-5-­(arylaminomethyl)-2-(methylthio)furo[2,3-d]pyrimidines via the Mitsunobu­ reaction of 4-amino-5-(hydroxymethyl)-2-(methylthio)furo[2,3-d]pyrimidine with N-mesyl- and N-nosylarylamines, and subsequent removal of the mesyl and nosyl groups, has been developed. The influence of substituents in the arylamine moiety on the Mitsunobu reaction was investigated. An unexpected nucleophilic substitution of a nitro group in the reaction of N-({4-amino-2-(methylsulfonyl)furo[2,3-d]pyrimidin-5-yl}methyl)-4-nitro-N-phenylbenzenesulfonamide with sodium methoxide was observed.

Key words

alkylation - sulfonamides - heterocycles - oxidation - nucleophilic aromatic substitution

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