Methyl 4-aminobenzoate → HCID 10133799, compound

Participants

Reaction Steps

Sodium hydride (22 mg, 0.93 mmol, 2.0 equiv) was added to a solution of methyl 4-aminobenzoate (140 mg, 0.93 mmol, 2.0 equiv) in DMF (5 mL) at 23° C. The resulting yellow solution was stirred for 15 minutes before 2-(methylsulfonyl)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidine (1-7, 140 mg, 0.47 mmol, 1 equiv) was added. The resulting red mixture was stirred for 30 minutes, then partitioned between brine (50 mL) and ethyl acetate (2×50 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (hexanes, initially, grading to 40% hexanes in ethyl acetate) to give methyl 4-{[4-(1-phenyl-1H-pyrazol-5-yl)pyrimidin-2-yl]amino}benzoate (2-1) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.41 (d, 1H, J=4.9 Hz), 7.86 (d, 2H, J=8.8 Hz), 7.78 (d, 1H, J=1.8 Hz), 7.52–7.33 (m, 5H), 7.28 (d, 2H, J=8.6 Hz), 6.90 (d, 1H, J=1.8 Hz), 6.78 (d, 1H, J=4.9 Hz), 3.90 (s, 3H)

Provenance & Evidence