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Short Paper | Regular issue | Vol 96, No. 7, 2018, pp.1248-1258
Published online, 26th June, 2018
DOI: 10.3987/COM-18-13911
Synthesis of 5-Hydroxythieno[2,3-d]pyrimidin-6(5H)-one Derivatives by the Reaction of 2-(4-Chloropyrimidin-5-yl)-2-hydroxyalkanoate with Sodium Hydrogensulfide

Kazuhiro Kobayashi,* Ikuma Murayama, Ryoga Ono, Daiki Fujiwara, Hidetaka Hiyoshi, and Kazuto Umezu

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


A convenient sequence for the preparation of 5-hydroxythieno[2,3-d]pyrimidin-6(5H)-one derivatives from 4,6-dichloro-2-(methylsulfanyl)pyrimidine (DCSMP) has been developed. Thus, 4,6-dichloro-5-lithio-2-(methylsulfanyl)pyrimidine, generated by the reaction of DCSMP with lithium diisopropylamide (LDA), was allowed to react with α-keto esters to afford 2-(4,6-dichloropyrimidin-5-yl)-2-hydroxyalkanoate derivatives. These underwent cyclization on treatment with sodium hydrogensulfide to give the corresponding 4-chloro-5-hydroxythieno[2,3-d]pyrimidin-6(5H)-one derivatives. After displacement of one of the two chloro groups of 2-(4,6-dichloropyrimidin-5-yl)-2-hydroxyalkanoate derivatives with methoxy, dialkylamino, or ethyl(or phenyl)sulfanyl groups, the resulting 2-(4-chloropyrimidin-5-yl)-2-hydroxyalkanoates were similarly treated with sodium hydrogensulfide to afford the corresponding desired products.