Water → HCID 68679889, compound

Participants

Reaction Steps

3-Benzylamino-propionic acid ethyl ester (2.0 g, 9.6 mmol) and 4-chloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (2.2 g, 9.6 mmol) were combined in DCM (50 mL) and triethylamine (1.5 g, 14.5 mmol) was added. After 14 h, water (25 mL) was added and the organic layer was separated, dried (MgSO4), and concentrated. Chromatography on silica (0-30% EtOAc/hexanes gradient) provided 2.91 g of 4-[benzyl-(2-ethoxycarbonyl-ethyl)-amino]-2-methylsulfanyl-pyridine-5-carboxylic acid ethyl ester. 1H NMR (400 MHz, CDCl3) δ (ppm): 8.46 (s, 1H), 7.23-7.33 (m, 5H), 4.75 (s, 2H), 4.21 (q, 2H, J=7.2 Hz), 4.06-4.15 (m, 2H), 3.77 (t, 2H, J=7.2 Hz), 2.66-2.70 (app t, 2H), 2.45 (s, 3H), 1.19-1.29 (m, 6H).

Provenance & Evidence