Water → HCID 68415195, compound

Participants

Reaction Steps

Diisopropylethylamine (0.59 ml, 3.39 mmol) was added to an N,N-dimethylformamide (2.7 ml) solution of 5-[2-amino-6-(2-aminoethylsulfanyl)pyrimidin-4-yl]-2,4-dimethylbenzoic acid methyl ester (225 mg, 0.68 mmol) obtained in Step 2 above, 4-tert-butoxycarbonylaminobutanoic acid (165 mg, 0.81 mmol), N-hydroxybenzotriazole (93 mg, 0.69 mmol), and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (262 mg, 1.37 mmol). The resulting mixture was stirred at room temperature for 2.5 hours. Water was added to the reaction solution, and extracted twice with ethyl acetate. The organic layers were combined together, and then sequentially washed with water and a saturated aqueous sodium chloride solution. The ethyl acetate solution was dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent: dichloromethane:methanol=30:1) to yield 5-{2-amino-6-[2-(3-tert-butoxycarbonylaminobutyrylamino)ethylsulfanyl]pyrimidin-4-yl}-2,4-dimethylbenzoic acid methyl ester (257 mg, 73%) as a white solid.

Provenance & Evidence