Benzylamine → Ammonium Hydroxide

Participants

Reaction Steps

The compound 3-[8-(2,6-difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylbenzoic acid (0.597 g, 1.35 mmol), benzyl amine (0.445 mL, 4.0 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.311 g, 1.62 mmol), 1-hydroxybenzotriazole hydrate (0.219 g, 1.62 mmol), were dissolved in CH2Cl2 (50 mL) and stirred under argon at room temperature for 16 h. The solvent was pumped off in vacuo. The reaction mixture was partitioned between ethyl acetate and water. The organic phase washed 3× with water, 1× brine, dried over anhydrous Na2SO4, filtered and evaporated. The crude product was flash chromatographed on silica gel (25 g) eluted with a gradient of 6:1:0.1, CH2Cl2:isopropanol:NH4OH to give the title compound. Crystallization from CH2Cl2/hexane gave the title compound as a white crystalline solid. m.p. (dec)154-159° C.; LC-MS m/z 532 (M+H)+, 2.24 min (ret. time).

Provenance & Evidence