Dimethylformamide → 5-{2-Amino-6-[3-(3-tert-butoxycarbonylaminopropoxy)phenylsulfanyl]pyrimidin-4-yl}-2-ethoxy-4-methylbenzoic acid methyl ester

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Reaction Steps

5-[2-Amino-6-(3-hydroxyphenylsulfanyl)pyrimidin-4-yl]-2-ethoxy-4-methylbenzoic acid methyl ester (110 mg, 0.27 mmol) obtained in Step 1 above, cesium carbonate (133 mg, 0.41 mmol), and N,N-dimethylformamide (1.2 ml) were added to a reaction vessel, and then 3-bromopropylcarbamic acid tert-butyl ester (97 mg, 0.41 mmol) was added thereto. The resulting mixture was stirred at room temperature for 4 hours. The reaction solution was diluted with ethyl acetate (100 ml), and sequentially washed twice with a saturated aqueous ammonium chloride solution (50 ml), twice with water (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: n-hexane:ethyl acetate=2:3) to yield 5-{2-amino-6-[3-(3-tert-butoxycarbonylaminopropoxy)phenylsulfanyl]pyrimidin-4-yl}-2-ethoxy-4-methylbenzoic acid methyl ester (145 mg).

Provenance & Evidence