(Diethylamino)sulfur trifluoride → 2-Chloro-4-(cyclopropyl(fluoro)methyl)pyrimidine

Participants

Reaction Steps

To a solution of (2-chloropyrimidin-4-yl)(cyclopropyl)methanol (75 mg, 0.406 mmol) in dichloromethane (2 mL) at 0° C. was added diethylaminosulfur trifluoride (66 mg, 0.410 mmol) and stirred for 30 min. The solution was concentrated to dryness and purified by flash chromatography on silica gel (0-100% EtOAc/hexanes) to afford 2-chloro-4-[cyclopropyl(fluoro)methyl]pyrimidine (20 mg, 0.107 mmol, 26% yield) as a colorless oil. MS ESI: [M+H]+ m/z 187.1. 1H NMR (500 MHz, CDCl3) δ 8.67 (d, J=5.0, 1H), 7.43 (d, J=5.0, 1H), 4.93 (dd, J=7.4, 47.5, 1H), 1.13 (m, 1H), 0.70-0.60 (m, 4H).

Provenance & Evidence