Triethylamine → (2S)-1-(4-{2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-9H-purin-8-yl}piperazin-1-yl)-1-oxopropan-2-ol

Participants

Reaction Steps

A methylene chloride (5 ml) solution of 5-{9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-8-piperazin-1-yl-9H-purin-2-yl}pyrimidin-2-amine (119 mg, 0.26 mmol), (S)-2-hydroxypropionic acid (28 mg, 0.32 mmol), 1-hydroxybenzotriazole (35 mg, 0.26 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (60 mg, 0.32 mmol), and triethylamine (55 μl, 0.39 mmol) was stirred at room temperature for 2 days. Chloroform and saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture and the resulting mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and, after filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (chloroform:methanol=96:4) to give a solid. The resulting solid was purified by flash NH silica gel column chromatography (methylene chloride:methanol=99:1) to give the title compound (63 mg, 46%) as a solid.

Provenance & Evidence