Dimethylformamide → HCID 178521260, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-(3-(3,5-dibromopyrazin-2-yl)ureido)acetate. 3,5-Dibromopyrazin-2-amine (5.00 g, 19.8 mmol), 1,1′-carbonyldiimidazole (3.37 g, 20.8 mmol), diisopropylethylamine (10.3 mL, 7.67 mmol), 1,4-dioxane (7.5 mL), and N,N-dimethylformamide (15 mL) were combined in a 100 mL round-bottom flask with a stirbar, stirred, and heated at 50° C. under a reflux condenser under nitrogen for 4.5 h. More 1,1′-carbonyldiimidazole (0.34 g, 2.08 mmol) was added and the reaction heated at 50° C. for an additional 3.5 h. The resulting reaction mixture was cooled to room temperature and glycine ethyl ester hydrochloride (2.90 g, 20.8 mmol) was added. The resulting reaction mixture was stirred at room temperature for 13 h at which time water was added with vigorous stirring to cause precipitation of solids. The solids were collected by vacuum filtration, washed twice with water and twice with hexane, and dried under vacuum at 45° C. to give the desired product (5.17 g, 68%) as a light orange solid which was contaminated with a small amount of ethyl 2-(3-(5-bromo-3-(1H-imidazol-1-yl)pyrazin-2-yl)ureido)acetate. 1H NMR (400 MHz, DMSO-d6) δ 8.89 (s, 1H) 8.53 (s, 1H) 8.08 (t, J=5.66, 1H) 4.12 (q, J=7.29, 2H) 3.96 (d, J=5.86, 2H) 1.21 (t, J=7.03, 3H); MS (ESI) m/z 383 [M+1]+.

Provenance & Evidence