Ethyl orthopropionate → 1-(7-bromo-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol

Participants

Reaction Steps

Pyridine hydrochloride (0.095 g, 0.82 mmol) and triethyl orthopropionate (6.36 g, 36.1 mmol) were sequentially added to a solution of 1-[(3-amino-7-bromo[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-ol (10.2 g, 32.8 mmol) in toluene (200 mL), and the resulting mixture was heated at reflux for three hours. Most of the solvent was removed under reduced pressure, and a solid was present. The solid was isolated by filtration and dried to provide 8.59 g of 1-(7-bromo-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol as a light yellow solid. A small portion of the solid was recrystallized from acetonitrile to provide an off-white solid, mp 207-208° C.

Provenance & Evidence