Triethylamine → 3-[5-chloro-2-methyl-4-(3-methyl-benzyloxy)-6-oxo-6H-pyrimidin-1-yl]-N-methoxy-4,N-dimethyl-benzamide

Participants

Reaction Steps

To a solution of 3-[5-chloro-2-methyl-4-(3-methyl-benzyloxy)-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid from Step C (220 mg, 0.56 mmol) in tetrahydrofuran (2 mL) was added 1,1′-carbonyldiimidazole (136 mg, 0.84 mmol). After stirring at ambient temperature for one hour, N,N-dimethylhydroxylamine HCl (81 mg, 0.84 mmol) and triethylamine (0.15 mL, 1.12 mmol) were added. The solution continued to stir for eighteen hours. The solution was partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium bicarbonate, water, 5% citric acid and brine and dried over magnesium sulfate. The slurry was filtered and concentrated to provide the amide as a brown oil (193 mg, 78%). MS (M+H): 442

Provenance & Evidence