4-Chloro-6-ethoxy-2-(methylthio)pyrimidine

Abstract

4,6-Dichloro-2-(methylthio)pyrimidine (3) reacts with EtONa in EtOH, at ca. 20 • C, for 2 h, to give exclusively 4-chloro-6-ethoxy-2-(methylthio)pyrimidine (5) in 89% yield. The latter is presented as a useful multifunctionalised pyrimidine scaffold.

Reactions of Polychlorinated Pyrimidines with DABCO

“…We are interested in studying the use of trichloropyrimidine 1 as a synthetic scaffold as it offers multiple sites of reactivity towards heteroatom nucleophiles or organometallic reagents. Previous efforts to access pyrimidine 1 involve the use of the starting material 4,6-dichloro-2-(methylthio)-pyrimidine (3) [16,17]. Another potentially useful scaffold for accessing pyrimidine 1 is the readily available 2,4,5,6-tetrachloropyrimidine (4), prepared by the treatment of barbituric acid with a refluxing mixture of PCl 5 and POCl 3 in 67% yield [18].…”