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

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Reaction Steps

5-(2-Amino-6-chloropyrimidin-4-yl)-2-methoxy-4-methylbenzoic acid methyl ester (154 mg, 0.5 mmol) obtained in Example 1-2 and 3-hydroxybenzenethiol (0.25 ml, 2.5 mmol) were placed in a reaction vessel, and then N,N-dimethylformamide (1.0 ml) and triethylamine (0.35 ml, 2.5 mmol) were added thereto. The solution was stirred at room temperature for 24 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. After filtration, the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent: ethyl acetate) to yield 5-[2-amino-6-(3-hydroxyphenylsulfanyl)pyrimidin-4-yl]-2-methoxy-4-methylbenzoic acid methyl ester (170 mg) as a yellow solid material.

Provenance & Evidence