反应详情

温度

10 °C

11.2 g (0.28 M) of 60% sodium hydride was suspended in 100 ml of N,N-dimethylformamide. While the suspension was cooled to 10° C. or lower in an ice water bath and stirred, thereto was dropwise added a solution of 25 g (0.14 M) of 2-(4,6-dimethoxypyrimidine-2-yl)acetonitrile dissolved in 100 ml of N,N-dimethylformamide. After the completion of the dropwise addition, the mixture was stirred at room temperature until there was no evolution of hydrogen. While the mixture was cooled to 10° C. or lower in an ice water bath and stirred, thereto was dropwise added a solution of 28 g (0.14 M) of 2-chloro-6-methoxymethylnitrobenzene dissolved in 100 ml of dimethylformamide. Then, the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into ice water. The mixture was acidified with 10% hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and water, dried and concentrated under reduced pressure. The resulting crystals were washed with a mixed solvent of ethanol and isopropyl ether to obtain 31 g (yield: 64%) of 2-(4,6-dimethoxypyrimidine-2-yl)-2-(3-methoxymethyl-2-nitrophenyl)acetonitrile as a reddish brown powder (melting point: 112 to 113° C).

1. additionAfter the completion of the dropwise addition
2. stirringthe mixture was stirred at room temperature until there
3. temperatureWhile the mixture was cooled to 10° C. or lower in an ice water bath
4. stirringstirred
5. stirringThen, the mixture was stirred at room temperature for 12 hours
6. extractionfollowed by extraction with ethyl acetate
7. washThe organic layer was washed with a saturated aqueous sodium chloride solution and water
8. customdried
9. concentrationconcentrated under reduced pressure
10. washThe resulting crystals were washed with a mixed solvent of ethanol and isopropyl ether