反应详情

To a solution of [10 g, 65.1 mmol] of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine in 250 mL of dry THF was cautiously added portionwise over 5 minutes time [2.86 g, 71.6 mmol] sodium hydride (60% oil dispersion). Reaction was then allowed to stir for 30 minutes at ambient temperature under a blanket of nitrogen gas. [12.96 g, 68.0 mmol] of solid toluene sulphonyl chloride was then added, in one portion and the reaction mixture was allowed to stir for one hour additional at ambient temperature. Ten mL of water was then cautiously added to the reaction (a quench for the excess hydride) and the solvent was removed under reduced pressure to ¼ the original volume. The residue was then suspended in 300 mL of water, stirred at ambient temperature for 30 minutes and isolated as a white solid via suction filtration. The material was washed with additional water and the damp cake was suspended in a minimum of acetonitrile and stirred overnight at ambient temperature. The precipitate was isolated via suction filtration and washed cautiously with cold acetonitrile and washed with hexanes; material air dried. Yield: 17.2 g of an off white solid (85%).

1. customReaction
2. stirringto stir for one hour additional at ambient temperature
3. customa quench for the excess hydride) and the solvent
4. customwas removed under reduced pressure
5. stirringstirred at ambient temperature for 30 minutes
6. customisolated as a white solid via suction filtration
7. washThe material was washed with additional water
8. stirringstirred overnight at ambient temperature
9. customThe precipitate was isolated via suction filtration
10. washwashed cautiously with cold acetonitrile
11. washwashed with hexanes
12. custommaterial air dried