Hydrochloric Acid → 1-(6-Chloropyrimidin-4-yl)ethan-1-one

Participants

Reaction Steps

4-Chloro-6-[1-(ethyloxy)ethenyl]pyrimidine (Intermediate 17, 564 mg, 3.05 mmol) was dissolved in acetone (15 mL), treated with 2M aqueous hydrochloric acid solution (2.291 mL, 4.58 mmol) and the resulting mixture was stirred at room temperature for 2.5 hours. A further amount of 2M aqueous hydrochloric acid solution (2.291 mL, 4.58 mmol) was added and the resulting mixture was stirred at room temperature for 18 hours. The solvent was removed under reduced pressure, the residue taken up in DCM and washed with saturated sodium bicarbonate solution. The DCM layer was separated and the aqueous layer was extracted with DCM (×2). The DCM layers were separated, combined, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Biotage SP4) eluting with a gradient of 0-30% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as a white solid (32 mg);

Provenance & Evidence