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温度

0 °C

5-Bromo-2-chloro-2,4-dimethoxy-pyrimidine (980 mg, 3.87 mmol) and 3-cyanomethyl-5-methyl-benzonitrile (666.4 mg, 4.26 mmol) were dissolved in dimethyl formamide (10 mL) at room temperature. The solution was cooled to 0° C. Sodium hydride in mineral oil (60%, 170 mg, 4.26 mmol) was added, the reaction mixture was allowed to warm to room temperature and stirring was continued. After 18 hours, a second batch of sodium hydride suspension in mineral oil (60%, 170 mg, 4.26 mmol) was added and stirring was continued for 30 minutes. The reaction was placed under an atmosphere of oxygen and stirring at room temperature was continued. After 72 hours, the reaction was quenched with aqueous ammonium chloride solution and extracted with diethyl ether. The combined organic layers were dried over sodium sulfate. Filtration and evaporation of solvents yielded the crude material. The crude material was purified by flash chromatography on silica gel (eluent: ethyl acetate in hexanes) to yield the product (445 mg, 1.23 mmol). 1H (CDCl3): δ=7.93 (s, 1H), 7.87 (s, 1H), 7.70 (s, 1H), 4.13 (s, 3H), 3.98 (s, 3H), 2.46 (s, 3H) ppm.

1. temperatureto warm to room temperature
2. stirringstirring
3. waitwas continued for 30 minutes
4. stirringstirring at room temperature
5. waitAfter 72 hours
6. customthe reaction was quenched with aqueous ammonium chloride solution
7. extractionextracted with diethyl ether
8. dry with materialThe combined organic layers were dried over sodium sulfate
9. filtrationFiltration and evaporation of solvents
10. customyielded the crude material
11. customThe crude material was purified by flash chromatography on silica gel (eluent: ethyl acetate in hexanes)