tert-Butanol → [4-(1-phenyl-1H-pyrazol-5-yl]pyrimidin-2-yl}amino benzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 4-{[4-(1-phenyl-1H-pyrazol-5-yl)pyrimidin-2-yl]amino}benzoate (2-1, 60 mg, 0.16 mmol, 1 equiv) and aqueous 1N sodium hydroxide solution (0.81 mL, 0.81 mmol, 5.0 equiv) in a 1:1 mixture of t-butanol and dioxane (5 mL) was heated at 80° C. for 16 hours. The reaction mixture was partitioned between aqueous half-saturated ammonium chloride solution and ethyl acetate (2×50 mL). The combined organic layers were dried over sodium sulfate and concentrated to give 4-{[4-(1-phenyl-1H-pyrazol-5-yl)pyrimidin-2-yl]amino}benzoic acid (2-2) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 12.50 (br s, 1H), 10.04 (s, 1H), 8.60 (d, 1H, J=4.9 Hz), 7.86 (s, 1H), 7.63 (d, 2H, J=8.2 Hz), 7.51–7.33 (m, 5H), 7.25 (d, 2H, J=8.6 Hz), 7.06 (m, 2H).

Provenance & Evidence