Imidazole → Pyrimidine, 2-(1,1-difluoro-2-iodoethyl)-

Participants

Reaction Conditions

Reaction Steps

A homogeneous solution of 2,2-difluoro-2-pyrimidin-2-yl-ethanol (689 mg, 4.31 mmol), as prepared in the previous step, PPh3 (1.69 g, 6.44 mmol), and imidazole (590 mg, 8.67 mmol) in toluene (5.8 mL) and CH3CN (2.9 mL) was stirred at 0° C. for 5 min, and was then treated with I2 (1.61 g, 6.34 mmol) in two portions and stirred at 0° C. for another 5 min. The resulting brown opaque slurry was then heated at 90° C. for 19 h, and then allowed to cool to rt. The mixture was filtered, the beige filter cake was washed with toluene (3×10 mL), and the combined brown filtrates were concentrated. Silica flash chromatography of the residue (2:1 hex/EtOAc eluent) afforded the title compound as a pale yellow oil (849 mg, 73%).

Provenance & Evidence