3-Chloroaniline → N-(3-chlorophenyl)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(methylsulfonyl)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidine (1-7, 96 mg) and 3-chloroaniline (0.5 mL, excess) was heated at 100° C. for 24 hours. The residue was purified by flash column chromatography (hexanes, initially, grading to 40% hexanes in ethyl acetate) to give N-(3-chlorophenyl)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidin-2-amine (1-8) as an off-white foam. 1H NMR (300 MHz, CDCl3) δ 8.37 (d, 1H, J=5.2 Hz), 7.78 (d, 1H, J=1.8 Hz), 7.56 (m, 1H), 7.46–7.32 (m, 5H), 7.12 (m, 1H), 7.08 (m, 1H), 6.96 (m, 1H), 6.92 (d, 1H, J=1.8 Hz), 6.66 (d, 1H, J=5.2 Hz).

Provenance & Evidence