4-Toluenesulfonyl chloride → Tert-butyl 5-bromopyrimidine-2-carboxylate

Participants

Reaction Steps

A suspension of 5-bromopyrimidine-2-carboxylic acid (690 mg, 3.40 mmol) in 6.8 mL t-BuOH and 1.9 mL pyridine was stirred at room temperature to 50° C. for 1 hr, and cooled to room temperature. 4-Toluenesulfonyl chloride (1.55 g, 8.12 mmol) was added portion wise. The mixture was stirred at room temperature for 1.5 h. The reaction was quenched with saturated aqueous NaHCO3 slowly, extracted with 3×Et2O, dried over Na2SO4, and concentrated. The residue was purified by Biotage column chromatography with 15-25% EtOAc in hexanes to give a yellow solid (497 mg, 56% yield). 1H NMR (400 MHz, CDCl3) δ 8.94 (s, 2 H) 1.64 (s, 9 H).

Provenance & Evidence