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

Participants

Reaction Steps

4,6-Dichloropyrimidine (2.0 g, 13.42 mmol) was dissolved in THF (10 mL), treated with sodium thiomethoxide (0.988 g, 14.10 mmol) and the resulting mixture was stirred at room temperature under argon for 18 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and brine. The ethyl acetate layer was separated, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Biotage SP4) eluting with a gradient of 0-20% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the desired product as a white solid (623 mg);

Provenance & Evidence