Sodium Carbonate → Methyl 5-bromo-2-isopropylpyrimidine-4-carboxylate

Participants

Reaction Steps

To a stirred, cooled (0° C.) solution of 5-bromo-2-isopropyl-pyrimidine-4-carboxylic acid (3 g, 12.2 mmol) in methanol (50 ml) under an argon atmosphere was added dropwise thionyl chloride (4.37 g, 2.68 ml, 36.7 mmol). When the addition was complete, the mixture was allowed to warm to rt and stirring at rt was continued for 17 h. The orange mixture was concentrated to leave a paste which was taken up in EtOAc (50 ml)/saturated aqueous Na2CO3 solution (50 ml). The aqueous phase was extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried over MgSO4, filtered and concentrated to leave the product (2.98 g, 94%) as a light brown oil which was used in the next reaction step without further purification.

Provenance & Evidence