Carbon Dioxide → HCID 117821330, compound

Participants

Reaction Steps

(2-Chloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-yl)methyl methanesulfonate (0.47 g, 1.40 mmol) was dissolved in benzene (8 mL). Cyclopropylmethanol (0.222 mL, 2.81 mmol), 5 M sodium hydroxide (0.421 mL, 2.11 mmol) and tetrabutylammonium hydrogen sulfate (48 mg, 0.14 mmol) were added. The mixture was stirred vigorously at ambient temperature for 3 h. Solid carbon dioxide was added followed by brine and water. The mixture was extracted twice with ethyl acetate, the organic phase was separated and dried over sodium sulfate. The solution was concentrated in vacuum, and the residue was purified by column chromatography on silica eluting with a gradient of 0-50% of ethyl acetate in heptane. The solvents were evaporated and the residue was purified by preparative HPLC to give the title compound, 33 mg (7.5%).

Provenance & Evidence