Pyridine → 5-(Bromoacetamido)-3-methyl-6-phenyl-[1,2,4]triazine

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Reaction Steps

To a solution of 5-amino-3-methyl-6-phenyl-[1,2,4]triazine (Example 25, step b); 550 mg, 2.96 mmol) in dichloromethane was added bromoacetyl bromide (0.308 ml, 3.55 mmol), pyridine (0.357 ml, 4.44 mmol) and 4-dimethylaminopyridine (10 mg). The reaction mixture was stirred under nitrogen at room temperature for 2 h, then evaporated in vacuo. The residue was purified by flash chromatography (SiO2; 40% ethyl acetate in hexanes) to yield 5-(bromoacetamido)-3-methyl-6-phenyl-[1,2,4]triazine (475 mg), m/z (ES+) 307/309 (M++H). To a solution of this product (470 mg, 1.53 mmol) in 1,2-dichloroethane was added triethylamine (0.235 ml, 1.68 mmol) and sodium iodide (10 mg), and the mixture was heated at reflux for 4 h. On cooling the title compound crystallised out of solution and was collected by filtration to yield 220 mg. δH (400 MHz; d6-DMSO) 2.80 (3H, s), 7.34 (1H, s), 7.56 (3H, m), 8.54 (2H, m), 11.35 (1H, bs); m/z (ES+) 227 (M++H).

Provenance & Evidence