Dimethylamine → N,N-dimethyl-5-nitro-1H-pyrazolo[3,4-b]pyridin-3-amine

HRID 1943887Notes

Reaction equation

HRID 1943887 reaction equation
[CH3:1][NH:2][CH3:3].O.Br[C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[NH:8][N:7]=1>CN(C=O)C.C(OCC)(=O)C>[CH3:1][N:2]([CH3:3])[C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[NH:8][N:7]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 178526791HCID 178526791, compound

Product 1

HCID 58227806N,N-dimethyl-5-nitro-1H-pyrazolo[3,4-b]pyridin-3-amineYield 22%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

40% Dimethyl amine in water (2.6 mL, 21 mmol) was added to a solution of 3-bromo-5-nitro-1H-pyrazolo[3,4-b]pyridine (0.063 g, 0.26 mmol) in DMF (6.0 mL), and the mixture was placed in a microwave reactor at 140° C. for 15 hours. The reaction mixture was diluted with ethyl acetate (100 mL), and the organic layer was washed with water (3×50 mL). The organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (4:1) to give N,N-dimethyl-5-nitro-1H-pyrazolo[3,4-b]pyridin-3-amine (0.012 g, 22%) as a solid.

Workup

  1. washthe organic layer was washed with water (3×50 mL)
  2. customThe organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography
  6. washeluting with hexanes/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-5bd89c0462394fbc80ca80d1bfa47ca7
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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