Ammonia → (S)-2-(1H-Benzo[d][1,2,3]triazol-1-yloxy)-4-(1-(5-fluoropyridin-2-yl)ethylamino) pyrimidine-5-carboxamide

Participants

Reaction Steps

N-(3-Dimethylaminopropyl)-N′-ethyl carbodiimide hydrochloride (177 mg, 0.92 mmol) and 1-hydroxybenzotriazole (125 mg, 0.93 mmol) were added to a solution of (S)-2-chloro-4-(1-(5-fluoropyridin-2-yl)ethylamino)pyrimidine-5-carboxylic acid (Preparation 5b, 210 mg, 0.62 mmol) in N,N′-dimethylformamide (5 mL) and the mixture was stirred for 30 min at ambient temperature. 0.5M Ammonia solution in 1,4-dioxane (3 mL) was then added and the reaction mixture was stirred overnight at ambient temperature. The solvents were evaporated and the resulting residue was taken up in diethyl ether. The organic solution was washed with water and brine, dried (Na2SO4), filtered and the solvent evaporated under reduced pressure. The residue was purified by reverse phase chromatography (C-18 silica from Waters©, water/acetonitrile/methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%) to yield the title compound (30 mg, 12%) as a solid.

Provenance & Evidence