Ethanolamine → 2-[(3-Bromoimidazo[1,2-a]pyrazin-8-yl)amino]ethan-1-ol

Participants

Reaction Conditions

Reaction Steps

3-Bromo-8-chloro-imidazo[1,2-a]pyrazine (0.70 g, 3.0 mmol) (from Example 1 supra) was stirred in nBuOH (10 mL) and ethanolamine (0.22 mL, 3.65 mmol) followed by Hunig's base (1.04 mL, 6.0 mmol) Reaction mixture was then heated at 100° C. overnight. The mixture was concentrated to dryness and water was added (150 mL) followed by a saturated aqueous solution of NaHCO3 (50 mL). The reaction was then extracted with EtOAc (3×20 mL) and the organic phases were combined, washed with water (2×20 mL), dried over MgSO4 and concentrated to dryness to give 2-(3-bromo-imidazo[1,2-a]pyrazin-8-ylamino)-ethanol. (Yield 0.59 g, 77%). 1H (400 MHz; DMSO-d6) δ 3.52-3.56 (2 H, m), 3.58-3.62 (2 H, m), 4.79 (1 H, t, J=5.4 Hz), 7.42 (2 H, d, J=5 Hz), 7.56 (1 H, d, J=5 Hz), 7.66 (1 H, s).

Provenance & Evidence