Isobutylamine → 5-Methyl-7-isobutylamino-1H-pyrazolo[4,3-b]pyridine

HRID 637985Notes

Reaction equation

HRID 637985 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[CH:9]=[N:10][NH:11][C:3]=12.[CH2:12]([NH2:16])[CH:13]([CH3:15])[CH3:14]>O.C(O)C>[CH3:8][C:6]1[N:5]=[C:4]2[CH:9]=[N:10][NH:11][C:3]2=[C:2]([NH:16][CH2:12][CH:13]([CH3:15])[CH3:14])[CH:7]=1

Participants

5

Reactant 2

HCID 6558IsobutylamineHCID 116798717-Chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 202548525-Methyl-7-isobutylamino-1H-pyrazolo[4,3-b]pyridineYield 40.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 7-chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine (1.0 g, 0.006 mole) and isobutylamine (58 g) in water (100 ml) and ethanol (50 ml) was heated under reflux for 10 days. The reaction mixture was cooled and evaporated to dryness. The oily residue was basified to pH8-9 with 10% sodium carbonate solution. The residue was extracted with ethyl acetate (3×100 ml), dried (Na2SO4) and evaporated to dryness to give a yellow oil. This was purified by column chromatography on alumina, and eluted with chloroform/methanol to give the desired compound as a white solid (500 mg). m.p. 162°-164° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 days
  3. temperatureThe reaction mixture was cooled
  4. customevaporated to dryness
  5. extractionThe residue was extracted with ethyl acetate (3×100 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness
  8. customto give a yellow oil
  9. customThis was purified by column chromatography on alumina
  10. washeluted with chloroform/methanol

Sources & evidence

ORD record
ord-1e35a82176b84261aec90207eee6f937
Source dataset
uspto-grants-1985_12
Patent number
US04559348

Reaction notes

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