Aniline → VE-821

Participants

Reaction Steps

A mixture of 3-amino-6-(4-methylsulfonylphenyl)pyrazine-2-carboxylic acid (1.5 g, 5.114 mmol), diethoxyphosphorylformonitrile (926.8 mg, 849.5 μL, 5.114 mmol), aniline (476.2 mg, 465.9 μL, 5.114 mmol) and triethylamine (1.035 g, 1.426 mL, 10.23 mmol) was stirred in DME (18.75 mL) at 120° C. for 18 hours. After this time water was added and the resultant solid collected by filtration and triturated with acetone to give the desired product (1.88 g, 71% Yield). 1H NMR (400.0 MHz, DMSO) δ 10.47 (s, 1H), 9.04 (s, 1H), 8.51 (d, J=8.4 Hz, 2H), 8.01 (d, J=8.4 Hz, 2H), 7.89 (s, 2H), 7.82 (d, J=7.9 Hz, 2H), 7.41 (t, J=7.8 Hz, 2H), 7.18 (t, J=7.3 Hz, 1H) and 3.28 (s, 3H) ppm; MS (ES+) 369.0.

Provenance & Evidence