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Paper | Regular issue | Vol 91, No. 6, 2015, pp.1177-1185
Published online, 21st April, 2015
DOI: 10.3987/COM-15-13202
Two-Step Synthesis of 5-Hydroxy-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one Derivatives from 4-Chloro-6-methoxy-2-(methylsulfanyl)pyrimidine

Kazuhiro Kobayashi,* Ryoga Ono, Shohei Yuba, Hidetaka Hiyoshi, and Kazuto Umezu

*Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

We report a facile two-step procedure that allows the synthesis of the title fused heterocyclic derivatives from 4-chloro-6-methoxy-2- (methylsulfanyl)pyrimidine, readily available from 4,6-dichloro-2-(methylsulfanyl)pyrimidine (DCSMP). The first step is the lithiation at the 5-position of the starting material with lithium diisopropylamide (LDA) and the reaction of the resulting lithium compound with α-keto esters to give the corresponding 2-hydroxy-2-(pyrimidin-5-yl)carboxylic acid ester derivatives. In the second step, these are treated with primary aliphatic amines in the presence of triethylamine to afford the desired products.