反应详情

Acetaldehyde (0.258 g, 5.86 mmol) and a drop of acetic acid were added to a solution of 5-nitro-1H-pyrazolo[3,4-b]pyridin-3-amine (0.105 g, 0.586 mmol) in THF/dichloroethane (“DCE”) (12 mL, 1:1). NaBH(OAc)3 (1.24 g, 5.86 mmol) was added, and the mixture was left at room temperature for 60 hours. The reaction mixture was diluted with ethyl acetate (50 mL) and quenched with water (10 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (9:1), hexanes/ethyl acetate (4:1) to give N,N-diethyl-5-nitro-1H-pyrazolo[3,4-b]pyridin-3-amine (22 mg, 16% yield) as a solid.

1. customquenched with water (10 mL)
2. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
3. customThe combined organic layers were dried
4. filtrationfiltered
5. concentrationconcentrated
6. customThe crude product was purified by column chromatography
7. washeluting with hexanes/ethyl acetate (9:1), hexanes/ethyl acetate (4:1)