反应详情

温度

0 °C

60% Sodium hydride in mineral oil (1.013 g, 25.34 mmol) was added to (S)-methyl 3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-hydroxypropanoate (Intermediate AB3) (8.5 g, 21.12 mmol) in tetrahydrofuran (150 mL) cooled to 0° C. under nitrogen. The resulting solution was stirred at 0° C. for 10 minutes. A solution of 4-chloro-1-(3-chloropyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidine (6.18 g, 23.23 mmol) in tetrahydrofuran (20 mL) was added dropwise over a period of 5 minutes. The resulting mixture was allowed to warm to ambient temperature and stirred for 2 hours. The reaction mixture was quenched with 1M citric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated. The crude product was purified by flash silica chromatography, eluting with 0 to 100% ethyl acetate in isohexane to afford the product (7.15 g, 53.6%).

1. temperatureto warm to ambient temperature
2. stirringstirred for 2 hours
3. customThe reaction mixture was quenched with 1M citric acid
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed with brine
6. dry with materialdried (MgSO4)
7. customevaporated
8. customThe crude product was purified by flash silica chromatography
9. washeluting with 0 to 100% ethyl acetate in isohexane