Phosphorus oxychloride → Ethyl 4-chloro-6-methyl-2-(methylsulfanyl)pyrimidine-5-carboxylate

Participants

Reaction Steps

A mixture of compound C (60 g; 0.263 mol) and POCl3 (300 mL) was vigorously stirred under reflux temperature for 2 h. Then POCl3 was distilled off under vacuum, the crude solid triturated with water and ethyl acetate and filtered on a Celite pad. The filtrate was neutralized with sodium bicarbonate and extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of sodium bicarbonate, washed with brine and dried over anhydrous sodium sulphate. After concentration the crude reaction mixture was purified by silica gel column chromatography (eluant: n-hexane/ethyl acetate=9/1) to yield compound D (31.8 g; 49%) as an orange oil.

Provenance & Evidence