Hydrochloric Acid → 2-Chloro-7H-pyrrolo[2,3-d]pyrimidine

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Reaction Conditions

Reaction Steps

A 500 mL round bottomed flask was charged with 2-Chloro-5-(2-ethoxyvinyl)-pyrimidin-4-ylamine 2 (4.4 g, 20 mmol). Isopropanol (200 mL) is added followed by 25 mL of concentrated hydrochloric acid. The solution is heated to 90° C. and stirred for two hours. After cooling to room temperature, the solution is concentrated under reduced pressure then basified to pH 9 with saturated aqueous NaHCO3. The aqueous layer is extracted with ethyl acetate, and the organic extracts are combined and washed with saturated aqueous NaHCO3 and brine. The organic extracts are dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by short-filtration (SiO2, Hexanes:Ethyl acetate/1:1) gives 3 (3.1 g, 92%) as a white solid.

Provenance & Evidence