Diethyl Ether → 2-(5-Bromopyrimidin-2-yl)propan-2-ol

Participants

Reaction Steps

To an ice-cold solution of methyl 5-bromopyrimidine-2-carboxylate (10 g, 46.1 mmol) in Et2O (200 mL) was added drop wise methyl magnesium bromide (3.0 M in Et2O, 61.4 mL, 184 mmol) over 30 min. The reaction mixture was slowly warmed up to RT and continued to stir for 2 h. The mixture was quenched with saturated NH4Cl solution at 0° C. and the organic layer separated from the biphasic solution. The aqueous layer was re-extracted with EtOAc (2×250 mL). The combined organic layers were washed with brine solution, dried over Na2SO4, filtered and evaporated in vacuo. The crude residue was purified over silica eluting with 20% EtOAc:hexane to obtain i (6.0 g, 62%). 1HNMR (DMSO-d6, 400 MHz): δ 8.97 (s, 2H), 5.15 (s, 1H) and 1.47 (s, 6H).

Provenance & Evidence