Water → 6-(cyclobutylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde

HRID 1911728Notes

Reaction equation

HRID 1911728 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[N:13]=[C:12]2[N:14]([CH3:18])[N:15]=[C:16]([CH3:17])[C:11]2=[CH:10][C:9]=1[CH:19]=[O:20].[CH:21]1([CH2:25][NH:26][CH2:27][CH3:28])[CH2:24][CH2:23][CH2:22]1.O>CN(C=O)C.C(OCC)(=O)C>[CH:21]1([CH2:25][N:26]([CH2:27][CH3:28])[C:8]2[N:13]=[C:12]3[N:14]([CH3:18])[N:15]=[C:16]([CH3:17])[C:11]3=[CH:10][C:9]=2[CH:19]=[O:20])[CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 162286606-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehydeHCID 23366322(Cyclobutylmethyl)(ethyl)amine

Product 1

HCID 574444326-(cyclobutylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehydeYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Potassium carbonate (0.83 g, 6 mmol) was added to a solution of 6-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (1.04 g, 5.0 mmol) and cyclobutylmethyl-ethyl-amine (0.8 g, 7.0 mmol) in anhydrous DMF (8 mL) under nitrogen. After stirring for 0.5 h at RT, the reaction mixture was heated for 14 h at 80° C. Thereafter, the reaction was cooled to RT, water (30 mL) and ethyl acetate (30 mL) were added, and the organic layer was separated from the aqueous mixture. The organic extract was washed with brine, dried over sodium sulfate and the solvent was evaporated in vacuo. The residue was purified by chromatography using silica gel (200-400 mesh) and eluted with 20-60% hexane:ethyl acetate to afford the title compound as a pale yellow liquid (1.23 g, yield: 87%).

Workup

  1. temperaturethe reaction mixture was heated for 14 h at 80° C
  2. temperatureThereafter, the reaction was cooled to RT
  3. customthe organic layer was separated from the aqueous mixture
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customThe residue was purified by chromatography
  9. washeluted with 20-60% hexane

Sources & evidence

ORD record
ord-38d8ccd0553a42baa947a930ddad4305
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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