反应详情

温度

0 °C

A solution of 1-(3,3-dimethylbutoxy)-8-(pyrimidin-5-yl)-10H-chromeno[3,2-c]pyridin-10-one (0.320 g, 0.852 mmol) in THF (8.00 mL) was cooled to 0° C. and methylmagnesium bromide (3.0 M in diethyl ether) (0.483 mL, 1.449 mmol) was added dropwise. The mixture stirred at 0° C. for 1 h. The mixture was quenched at 0° C. with saturated aqueous ammonium chloride solution and diluted with EtOAc. The aqueous phase was separated and extracted with EtOAc. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a yellow film. This material was dissolved in chloroform (8.00 mL), pyridinium p-toluenesulfonate (10.71 mg, 0.043 mmol) was added, and the mixture was heated at reflux for 2 h. The reaction mixture was diluted with DCM and the solution was partitioned between DCM and saturated aqueous sodium bicarbonate solution. The aqueous phase was separated and extracted with DCM. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 1-(3,3-dimethylbutoxy)-10-methylene-8-(pyrimidin-5-yl)-10H-chromeno[3,2-c]pyridine as a yellow solid. MS m/z=374.2 [M+H]+. Calcd for C23H23N3O2: 373.4.

1. customThe mixture was quenched at 0° C. with saturated aqueous ammonium chloride solution
2. additiondiluted with EtOAc
3. customThe aqueous phase was separated
4. extractionextracted with EtOAc
5. washThe combined organic phases were washed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customto afford a yellow film
10. temperaturethe mixture was heated
11. temperatureat reflux for 2 h
12. customthe solution was partitioned between DCM and saturated aqueous sodium bicarbonate solution
13. customThe aqueous phase was separated
14. extractionextracted with DCM
15. washThe combined organic phases were washed with brine
16. dry with materialdried over anhydrous sodium sulfate
17. filtrationfiltered
18. concentrationconcentrated