Oxygen → 3-(5-Cyclopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

Participants

Reaction Conditions

Reaction Steps

At 0° C., NaH (60%, 9 mg, 0.4 mmol, 2 eq.) was added to (5-cyclopropyl-2,6-dimethoxy-pyrimidin-4-yl)-(3,5-dimethyl-phenyl)-acetonitrile (67 mg, 0.2 mmol) in 2 mL DMF solution. Oxygen balloon was applied. The reaction was stirred at 0° C. and warmed up to room temperature overnight. LC-MS shows the reaction complete. Ethyl acetate was added to the reaction mixture, followed by washing with brine. The organic layer was concentrated down and purified (silica gel, 0-50% EtOAc/hexane) to give white solid (31 mg, 48%). LC-MS shows 324.2 (M+1). 1H NMR (300 MHz, CDCl3): δ 7.98 (s, 1H), 7.90 (s, 1H), 7.63 (s, 1H), 4.05 (s, 3H), 3.93 (s, 3H), 2.43 (s, 3H), 1.53 (m, 1H), 0.77 (m, 2H), 0.42 (m, 2H).

Provenance & Evidence