Carbon Dioxide → HCID 21935657, compound

Participants

Reaction Conditions

Reaction Steps

A 1.2 M solution of DIBALH in toluene (50 ml, 60 mmol) was dropped within 20 min to a dry ice cooled (−30° C.) solution of 4-(2-methoxy-ethyl)-2-(6-trifluoromethyl-pyridin-3-yl)-pyrimidine-5-carboxylic acid methyl ester and 4-(2-methoxy-ethyl)-2-(6-trifluoromethyl-pyridin-3-yl)-pyrimidine-5-carboxylic acid ethyl ester (6.83 g, 20 mmol) in THF (100 ml). The reaction mixture was warmed to 0° C., stirred for 1 h at this temperature, the cooling bath was removed and stirring was continued for 1 h at ambient temperature. The mixture was cooled to 0° C., neutralized with aqueous KHSO4 solution (10%) and extracted three times with ether. The combined extracts were washed with aqueous NaCl solution (10%), dried (Na2SO4) and the solvent was removed under reduced pressure. The crude product was crystallized (dichloromethane/ether, 0° C.) to give 6.72 g (21.4 mmol, quant.) [4-(2-methoxy-ethyl)-2-(6-trifluoromethyl-pyridin-3-yl) -pyrimidin-5-yl]-methanol.

Provenance & Evidence