4,6-Dichloropyrimidine → 4-Chloro-6-(methylsulfanyl)pyrimidine

Participants

Reaction Steps

A mixture of 4,6-dichloro-pyrimidine (20.93 g, 140 mmol) and sodium thiomethoxide (10.3 g, 147 mmol) in THF (100 mL) was stirred at room temperature for 16 h, then the reaction mixture was concentrated. The residue was partitioned between ethyl acetate and brine. The organic layer was separated and washed with brine, then dried over sodium sulfate and concentrated. The crude product residue was purified by recrystallization from hexanes (60 mL) to afford the title compound. The mother liquor was concentrated and the residue was purified by silica gel flash chromatography (0% to 10% ethyl acetate in hexanes as eluant) to afford additional title compound containing a small amount of byproduct 4,6-bis methylthio-pyrimidine. 1H NMR 400 MHz (CDCl3) δ 8.72 (s, 1H), 7.21 (s, 1H), 2.58 (s, 3H).

Provenance & Evidence