反应详情

Sparge a solution of 2-(but-3-yn-1-yloxy)-1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]ethanone (8.15 g, 21.7 mmol) and L-ascorbic acid sodium salt (8.58 g, 43.3 mmol) in dimethylformamide (60 mL) and water (60 mL) with nitrogen for ten minutes, then evacuate and backfill with nitrogen three times. Add copper (II) sulfate pentahydrate (1.08 g, 4.33 mmol) and heat to 90° C., then add azidotrimethylsilane (23.1 mL, 20.0 g, 173 mmol) dropwise and stir for one hour. Cool reaction mixture to 23° C. and pour into water (50 mL). Extract this mixture with ethyl acetate (4×50 mL). Combine the organic extracts and wash with saturated aqueous sodium chloride, dry over anhydrous sodium sulfate, filter, and concentrate. Purify the resulting crude product by silica gel column chromatography (gradient elution: 0 to 10% methanol in ethyl acetate) to give the title compound (3.60 g, 40%). MS (m/z): 420 (M+1).

1. customevacuate
2. temperatureCool
3. customreaction mixture to 23° C.
4. extractionExtract this mixture with ethyl acetate (4×50 mL)
5. washCombine the organic extracts and wash with saturated aqueous sodium chloride
6. dry with materialdry over anhydrous sodium sulfate
7. filtrationfilter
8. concentrationconcentrate
9. customPurify the resulting crude product
10. washby silica gel column chromatography (gradient elution: 0 to 10% methanol in ethyl acetate)