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Short Paper | Regular issue | Vol 96, No. 2, 2018, pp.287-296
Published online, 25th December, 2017
DOI: 10.3987/COM-17-13840
Synthesis of 6,7-Dihydro-5H-thiopyrano[2,3-d]pyrimidin-5-one Derivatives Starting with 4,6-Dichloro-2-(methylsulfanyl)pyrimidine

Kazuhiro Kobayashi,* Ryoga Ono, Kouki Ishitobi, Ikuma Murayama, 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


An efficient synthesis of 7-substituted 6,7-dihydro-5H-thiopyrano[2,3-d]pyrimidin-5-one derivatives from readily available 4,6-dichloro-2-(methylsulfanyl)pyrimidine (DCSMP) has been developed. Thus, this starting material is converted to the corresponding 1-(4-chloro-6-methoxy(or dialkylamino)pyrimidin-5-yl)alk-2-en-1-ones by using easily operational sequences. These enones are then treated with sodium hydrogensulfide under mild conditions to afford the desired products in satisfactory yields.