Hydrogen Bromide → Imidazo(1,2-a)pyrazine

Participants

Reaction Steps

2-Aminopyrazine (100 mg, 1.1 mmol) and bromoacetaldehyde dimethylacetal (253 mg, 1.6 mmol) were dissolved in ethanol (4.5 ml), hydrobromic acid (48%, 0.5 ml) added and the mixture was heated under reflux for 18 h. The solution was allowed to cool to room temperature then pre-adsorbed directly onto silica. Purification by silica gel chromatography eluting with dichloromethane and 1% conc. ammonia on a gradient of methanol (1-4%) gave imidazo[1,2-α]pyrazine (90 mg, 72%) as a white crystalline solid: δH (360 MHz, CDCl3) 6.70 (1H, s), 7.82 (1H, s), 7.88 (1H, d, J 4), 8.29 (1H, d, J 4), 9.12 (1H, s).

Provenance & Evidence