Phenethylamine → (5-chloro-6-methyl-2-oxo-3-phenethylamino-2H-pyrazin-1-yl)acetic acid benzyl ester

Participants

Reaction Steps

2-Phenethylamine (0.38 ml, 3.0 mmol) was added to a stirred mixture of (3,5-dichloro-6-methyl-2-oxo-2H-pyrazin-1-yl)acetic acid benzyl ester (327 mg, 1.00 mmol) in EtOAc (2 ml) and the resulting mixture was heated to reflux under argon. After 2 h the reaction was cooled, diluted with EtOAc (the product is sparingly soluble), washed with 10% citric acid solution and brine, dried (Na2SO4) and evaporated in vacuo to give 1-3 as a crystalline solid. 1H NMR (CDCl3) δ2.21 (s, 3 H, CH3), 2.93 (t, J=7.1 Hz, 2 H, PhCH2), 3.67 (q, J=7.1 Hz, 2 H, CH2NH), 4.79 (s, 2 H, CH2), 5.21 (s, 2 H, CH2), 6.10 (br t, 1 H), 7.20-7.39 (m, 10 H, 2 Ph).

Provenance & Evidence