HCID 46192921, compound → 1H-Pyrazolo[3,4-b]pyridin-5-amine

HRID 1943862Notes

Reaction equation

HRID 1943862 reaction equation
C[Si](C)(C)CCOC[N:7]1[C:11]2=[N:12][CH:13]=[C:14]([NH:16]C(=O)OC(C)(C)C)[CH:15]=[C:10]2[CH:9]=[N:8]1>Cl.O1CCOCC1>[NH:7]1[C:11]2=[N:12][CH:13]=[C:14]([NH2:16])[CH:15]=[C:10]2[CH:9]=[N:8]1

Participants

4

Reactant 1

HCID 46192921HCID 46192921, compound

Product 1

HCID 461929221H-Pyrazolo[3,4-b]pyridin-5-amineYield 97.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridin-5-ylcarbamate (0.100 g, 0.274 mmol) was dissolved in 4N HCl in dioxane (8 mL), and the reaction mixture was left at room temperature overnight. The reaction mixture was concentrated. The resulting solids were suspended in DCM and neutralized with triethylamine. The crude product was purified by column chromatography, eluting with ethyl acetate to give 1H-pyrazolo[3,4-b]pyridin-5-amine (0.036 g, 95%) as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe crude product was purified by column chromatography
  3. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-d60f2dda0e38470e80d50722d34caa74
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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