Ethylmorpholine → GW-842,166X

Participants

Reaction Steps

To a solution of 2-(2,4-dichlorophenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid (86 g) in dimethylformamide (800 ml) was added successively N-ethylmorpholine (93 ml), 4 aminomethyltetrahydropyran (29.5 g), 1-hydroxybenzotriazole hydrate (51.5 g) and 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (56.2 g). The solution was stirred for 24 h. Dimethylformamide was partially removed (approx 650 ml) under reduced pressure and 5% sodium bicarbonate solution added (3×500 ml, added portionwise to control the release of carbon dioxide). The mixture was stirred with overhead stirring for 3 h and the resulting solid filtered onto a sinter. The solid was washed with 5% sodium bicarbonate (4×400 ml) and water (3×400 ml) then dried over sodium hydroxide in vacuo at 50° C. to afford the title compound (109.1 g)

Provenance & Evidence