Nicotinic acid, hydrazide → 2-phenyl-5-(5-(pyridin-3-yl)-1H-1,2,4-triazol-3-yl)pyrimidine

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Reaction Steps

2-Phenyl-pyrimidine-5-carbonitrile (Biofine International, 0.20 g, 1.10 mmol) and nicotinic hydrazide (Aldrich, 0.151 g, 1.10 mmol) were dissolved in o-xylene (5 mL) and heated to 200° C. under nitrogen atmosphere for seven hours as the o-xylene slowly boiled off. The remaining crude solid was dissolved in a minimal amount of 98:2 v/v dichloromethane-methanol and purified by flash silica column chromatography. Elution through a 40-g Analogix® flash silica cartridge with 100% dichloromethane to 5% methanol in dichloromethane afforded the title compound as a yellow solid (32 mg, 10% yield); Rf 0.27 with 95:5 v/v dichloromethane-methanol; melting point 322-333° C.; 1H-NMR (400 MHz; CDCl3) δ 9.53 (s, 2H), 9.32 (d, 1H), 8.76-8.75 (m, 1H), 8.53-8.46 (m, 3H), 7.64-7.60 (m, 4H); MS (ESI+) m/z 301.1 (M+1); H-PGDS FPBA IC50: 1 μM.

Provenance & Evidence