Benzyl Alcohol → 3-(2,6-Bis-benzyloxy-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzonitrile

Participants

Reaction Conditions

Reaction Steps

At 0° C., NaH (60%, 118 mg, 2.88 mmol, 2.2 eq.) was added to benzyl alcohol (298 μL, 2.88 mmol) in 5 mL of THF solution. The reaction mixture was stirred at 0° C. for 5 minutes. 3-(2,6-Dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzonitrile (422 mg, 1.31 mmol) was added. The reaction mixture was stirred at 0° C. for 15 minutes, then warmed to room temperature for 90 minutes. Ethyl acetate was added to the reaction mixture, which was then washed with brine. The organic layer was concentrated and purified (silica gel, 0-50% EtOAc/hexane) to give a white solid (372 mg, 65% pure by HPLC, 40%). LC-MS shows 466.1 (M+1).

Provenance & Evidence