Water → 1-(4,6-Dichloropyrimidin-5-yl)ethan-1-ol

Participants

Reaction Conditions

Reaction Steps

Methylmagnesium bromide solution (1.4 M in toluene/tetrahydrofuran (75:25); 2.4 mL, 3.4 mmol) was added to a solution of 4,6-dichloro-pyrimidine-5-carbaldehyde (Intermediate 16; 500 mg, 2.8 mmol) in tetrahydrofuran at 0° C. under nitrogen. The reaction mixture was stirred at 0° C. for 10 min and then at room temperature for 30 min. Water was added and the mixture was extracted with ethyl acetate (3×25 mL). The organic layers were washed with water and brine, dried (sodium sulfate), filtered, and evaporated to give 1-(4,6-dichloro-pyrimidin-5-yl)-ethanol (540 mg, 100%) which was used directly in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 1.19 (d, 3H, J=6.3 Hz), 2.62 (br s, 1H), 5.48-5.54 (m, 1H), 8.68 (s, 1H).

Provenance & Evidence