Triethylamine → 4-Chloro-6-ethylpyrimidine

Participants

Reaction Steps

6-Ethyl-4-pyrimidinol (Intermediate 11, 0.93 g, 7.49 mmol) was treated with triethylamine (1.044 mL, 7.49 mmol) and phosphorus oxychloride (3.49 mL, 37.5 mmol) and the resulting mixture was heated under reflux for 2 hours. The reaction mixture was allowed to cool to room temperature, evaporated under reduced pressure and the residue was poured into 2M aqueous hydrochloric acid solution (10 mL). This solution was extracted with DCM (×2). The DCM layers were combined, 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 title compound as a colourless oil (552 mg);

Provenance & Evidence