Triethylamine → 1-(4-Trifluoromethylpyrimidin-5-yl)-1-(4-methoxypyrimidin-5-yl)-1-trimethylacetoxymethane

Participants

Reaction Steps

Trimethylacetyl chloride (36 μl, 35.1 mg, 0.28 mmol, 3.2 equivalent) was added via syringe to a solution of 1-(4-trifluoromethylpyrimidin-5-yl)-1-(4-methoxypyrimidin-5-yl)methanol (25.1 mg, 0.0877 mmol), triethylamine (70 μl, 50.5 mg, 0.50 mmol, 5.7 equivalents) and dimethylaminopyridine (DMAP) (cat.) in toluene (5 ml) and the solution heated to reflux for 2 hours. The solution was cooled, diluted with NaHCO3 (sat.), and extracted with EtOAc (3 times). The combined extracts were washed with brine (sat.), dried (MgSO4), filtered and concentrated in vacuo. Preparative thin layer chromatography (SiO2 ; hexane/EtOAc, 1:1) gave 26 mg of 1-(4-trifluoromethylpyrimidin-5-yl)-1-(4-methoxypyrimidin-5-yl)-1-trimethylacetoxymethane as a solid.

Provenance & Evidence