Dimethylformamide → 5-[2-Amino-6-(3-hydroxyphenylsulfanyl)pyrimidin-4-yl]-2-ethoxy-4-methylbenzoic acid methyl ester

Participants

Reaction Steps

5-(2-Amino-6-chloropyrimidin-4-yl)-2-methoxy-4-methylbenzoic acid methyl ester (96.5 mg, 0.3 mmol) obtained in Example 1-2 and 3-hydroxybenzenethiol (0.15 ml, 1.5 mmol) were placed in a reaction vessel, and then N,N-dimethylformamide (0.6 ml) and triethylamine (0.2 ml, 1.5 mmol) were added thereto. The solution was stirred at room temperature for 20 hours. The reaction solution was diluted with ethyl acetate (100 ml), and sequentially washed twice with water (50 ml), twice with a saturated aqueous sodium bicarbonate solution (50 ml), and with a saturated aqueous sodium chloride solution (50 ml). The washed ethyl acetate solution was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=1:1 to 1:2) to yield 5-[2-amino-6-(3-hydroxyphenylsulfanyl)pyrimidin-4-yl]-2-ethoxy-4-methylbenzoic acid methyl ester (110 mg) as a white solid material.

Provenance & Evidence