4-Chloro-6-hydrazinyl-2-methylpyrimidine → 4-chloro-6-(5-(3,4-dimethoxybenzyl)-1H-1,2,4-triazol-1-yl)-2-methylpyrimidine

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Reaction Steps

A solution of (Z)-2-(3,4-dimethoxyphenyl)-N-(1-(dimethylamino)ethylidene)acetamide (1-2, 90 mg, 0.360 mmol, 1.0 eq) and 4-chloro-6-hydrazinyl-2-methylpyrimidine (57 mg, 0.360 mmol, 1.0 eq) in acetic acid (3 ml) was heated at 90° C. for 30 min. The reaction appeared complete by LCMS. The reaction mixture was concentrated and partitioned between dichloromethane (10 mL) and saturated aqueous sodium bicarbonate solution (10 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel column chromatography (0-100% ethyl acetate in hexanes) to afford 4-chloro-6-(5-(3,4-dimethoxybenzyl)-1H-1,2,4-triazol-1-yl)-2-methylpyrimidine (1-3). 1H NMR (500 MHz, CDCl3) δ 7.99 (s, 1H), 7.79 (s, 1H), 6.80 (m, 3H), 4.74 (s, 2H), 3.84 (s, 3H), 3.83 (s, 311), 2.76 (s, 3H). LRMS m/z (M+H) 346.4 found, 346.1 required

Provenance & Evidence