Thionyl Chloride → 6-(chloromethyl)-N-(3,4-dichlorophenyl)pyrimidin-4-amine

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Reaction Steps

Thionyl chloride (0.184 mL, 2.52 mmol) was added dropwise to a stirred solution of (6-((3,4-dichlorophenyl)amino)pyrimidin-4-yl)methanol (0.17 g, 0.629 mmol) in chloroform at 0° C. The mixture was allowed to warm to room temperature and further stirred for 18 h. After concentration, the crude product 6-(chloromethyl)-N-(3,4-dichlorophenyl)pyrimidin-4-amine (0.08 g, 75%) was used in the next step without purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.85 (1H, br. s.), 8.81 (1H, s), 8.20 (1H, s), 7.64 (2H, s), 7.11 (1H, s), 4.76 (2H, s). LCMS: R.T.=3.48; [M+H]+=287.91.

Provenance & Evidence