反应详情

Into a solution of 1.00 g (2.71 mmol) of {5-[(2-chloro-3,5-dimethoxy-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl}-ethyl-amine in 7 mL of dry DMF cooled to 5° C. was added 0.271 g (6.78 mmol) of sodium hydride as a 60% mineral oil suspension. The ice bath was removed, and the reaction was stirred for 1 hour. To the reaction was then added 1.32 g (8.13 mmol) of 1,1′-carbonyldiimidazole. After stirring a further 2 hours, the reaction was concentrated in vacuo. The residue was partitioned between dichloromethane and a saturated solution of ammonium chloride. The aqueous layer was washed twice with dichloromethane. The dichloromethane layers were combined, dried over magnesium sulfate, and concentrated in vacuo. The residue was dissolved in dichloromethane, added silica gel, and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with dichloromethane/ethyl acetate (9:0.5 v/v), to give 0.7507 g (70%) of the title compound: mp 189-191° C.

1. customThe ice bath was removed
2. stirringAfter stirring a further 2 hours
3. concentrationthe reaction was concentrated in vacuo
4. customThe residue was partitioned between dichloromethane
5. washThe aqueous layer was washed twice with dichloromethane
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated in vacuo
8. dissolutionThe residue was dissolved in dichloromethane
9. additionadded silica gel
10. concentrationconcentrated in vacuo
11. customThe residue was chromatographed on silica gel
12. washeluting with dichloromethane/ethyl acetate (9:0.5 v/v)