Sodium borohydride → (4-Methoxypyrimidin-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 3.7 g (20.3 mMol) 4-methoxy-pyrimidine-2-carboxylic acid ethyl ester in 37 ml of tert-butanol, 2.3 g (61 mMol) of NaBH4 are added. The mixture is stirred at 60° C. for 5 h and cooled to rt. 15 min after quenching with 5 ml of acetone, the mixture is poured into 20 ml of a sat. NaHCO3 solution and 0.4 l EtOAc and stirred for 20 min. The inorganic phase is separated off and extracted twice with EtOAc. The organic layers are washed with 20 ml of a 1:1 mixture of brine and water, dried (Na2SO4) and concentrated, yielding (4-methoxy-pyrimidin-2-yl)-methanol (MS: [M+1]+=141).

Provenance & Evidence