Methyl chloroformate → 6-[(cyclopropylmethyl)(propyl)amino]-N-[3-(1H-1,2,4-triazol-1-yl)phenyl]pyrimidine-4-carboxamide

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Reaction Conditions

Reaction Steps

A cooled (0° C.) solution of 6-(cyclopropylmethyl(propyl)amino)pyrimidine-4-carboxylic acid (Intermediate 21, 112 mg; 0.45 mmol) in DCM was treated with diisopropylethylamine (78.4 mL; 0.52 mmol) and methyl chloroformate (36.2 mL; 0.47 mmol). After stirring at 0° C. for 15 minutes, 3-(1H-1,2,4-triazol-1-yl)aniline (Maybridge, 108 mg; 0.67 mmol) was added and the mixture stirred for 72 hours. The solvent was evaporated and the compound purified by preparative HPLC to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.16 (1H, s), 8.60 (2H, d, J=18.1 Hz), 8.37 (1H, s), 8.11 (1H, s), 7.68-7.64 (1H, m), 7.53-7.48 (2H, m), 7.36 (1H, s), 3.54 (4H, s), 1.75-1.65 (2H, m), 1.10 (1H, s), 0.97 (3H, t, J=7.3 Hz), 0.58 (2H, d, J=7.7 Hz), 0.36-0.30 (2H, m). MS (ESI+) 387. HPLC (Condition C) Rt 3.77 min (HPLC purity 99.9%).

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