1-Methylpiperazine → N-{4-[(4-methylpiperazin-1-yl)carbonyl]phenyl}-4-(1-phenyl-1H-pyrazol-5-yl) pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-{[4-(1-phenyl-1H-pyrazol-5-yl)pyrimidin-2-yl]amino}benzoic acid (2-2, 60 mg, 0.16 mmol, 1 equiv), 1-methylpiperazine (49 mg, 0.49 mmol, 3.0 equiv), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (47 mg, 0.24 mmol, 1.5 equiv), 1-hydroxy-7-azabenzotriazole (37 mg, 0.24 mmol, 1.5 equiv) in DMF (40 mL) was stirred for 20 hours at 23° C. The reaction mixture was partitioned between water (75 mL) and ethyl acetate (2×50 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by reverse-phase LC (H2O/CH3CN gradient w/0.1% TFA present) to provide N-{4-[(4-methylpiperazin-1-yl)carbonyl]phenyl}-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidin-2-amine (2-3) as an off-white solid. 1H NMR (300 MHz, DMSO-d6, TFA salt) δ 9.93 (s, 1H), 9.87 (br s, 1H), 8.59 (d, 1H, J=4.9 Hz), 7.86 (d, 1H, J=1.8 Hz), 7.51–7.33 (m, 5H), 7.23 (d, 2H, J=8.2 Hz), 7.17 (d, 2H, J=8.6 Hz), 7.06 (m, 2H), 4.20 (br m, 2H), 3.49 (br m, 2H), 3.28 (br m, 2H), 3.10 (br m, 2H), 2.85 (s, 3H).

Provenance & Evidence