Thionyl Chloride → 5-(chloromethyl)-N-(4-chlorophenyl)pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (0.427 mL, 5.86 mmol) was added to a suspension of (2-((4-chlorophenyl)amino)pyrimidin-5-yl)methanol (0.23 g, 0.976 mmol) in DCM (10 mL) cooled to 0° C. The mixture was stirred for 18 h while warming to room temperature. The reaction mixture was concentrated and the residue triturated with ether to give 5-(chloromethyl)-N-(4-chlorophenyl)pyrimidin-2-amine as a pale yellow solid (0.28 g, 99%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.03 (s, 1H), 8.60 (s, 2H), 7.85-7.64 (m, 2H), 7.41-7.20 (m, 2H), 4.77 (s, 2H).

Provenance & Evidence