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Paper | Regular issue | Vol 78, No. 9, 2009, pp.2263-2275
Published online, 1st May, 2009
DOI: 10.3987/COM-09-11715
Chemoselective Displacement of Methylsulfinyl Group with Amines to Provide 2-Alkylamino-4,6-disubstituted Pyrimidine-5-carboxylic Acid

Shigeki Seto* and Yasushi Kohno

*Discovery Research Laboratoires, Kyorin Pharmaceutical Co., Ltd., 2399-1 Nogi, Nogi-mcahi, Shimotsuga-gun, Tochigi, 329-0114, Japan

Abstract

An efficient and rapid method for introducing various kinds of alkylamines at C2 of methyl 6-(benzylamino)-4-chloro-2-(methylsulfinyl)pyrimidine-5-carboxylate using the chemoselective displacement of the methylsulfinyl group (SOMe) against a chlorine atom with amines was investigated. Further transformation led to the synthesis of 2-alkylamino-4,6-disubstituted pyrimidine-5-carboxylic acids that are of biological interest.