1,4-Dioxane → 2-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-(1-(2,2,2-trifluoroethoxy)ethyl)pyrimidin-4-yl)propan-2-ol

Participants

Reaction Steps

1-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-(1-(2,2,2-trifluoroethoxy)-ethyl)pyrimidin-4-yl)ethanone (120 mg, 0.27 mmol) was coevaporated with dioxane and dissolved in THF (5 mL). The mixture was added slowly to a vigorously stirred solution of methylmagnesium bromide (0.712 mL of 3M solution, 2.14 mmol). The mixture was stirred for 10 minutes. The mixture was cooled in an ice bath and slowly quenched with a saturated solution of ammonium chloride in water (10 mL). The mixture was extracted with ethyl acetate (2×20 mL). The organic phase was separated, dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound as a solid 81 mg (64%).

Provenance & Evidence