Methyl iodide → Methyl 4-(4-isopropoxyphenyl)-2-(4,6-dimethylpyrimidin-2-ylthio)nicotinate

참여 물질

반응 단계

20.0 g (0.059 mol) of 2-bromo-4-(4-isopropoxyphenyl)nicotinic acid and 5.5 g (0.072 mol) of thiourea were dissolved in 40 ml of 5% HCl and 60 ml of acetic acid, and stirred at 100° C. for 2 hours. The reaction mixture was poured into water, and 200 ml of 50% sodium hydroxide was added thereto, and the mixture was stirred at room temperature for 30 minutes. The mixture was then acidified with 20% HCl and the thus precipitated was filtrated out and washed with water and then dried. The above synthesized crude crystal [2-mercapto-4-(4-isopropoxyphenyl)nicotinic acid] and 11.1 g (0.060 mol) of 4,6-dimethyl-2-methylsulfonylpyrimidine, and 25.0 g (0.18 mol) of potassium carbonate were dissolved in 200 ml of dimethylsulfoxide and stirred at 80° C. for 2 hours. After restoring the temperature to room temperature, 16.8 g (0.12 mol) of methyl iodide was added to the reaction mixture, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was then poured into water, and was extracted with 500 ml of ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and concentrated. The concentrate was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1/2) to obtain 6.5 g of a light-yellowish thick syrup-like aimed product.

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