Triethylamine → 3-amino-1H-Pyrazolo[3,4-b]pyridine-5-carbonitrile

HRID 398347

Reaction equation

HRID 398347 reaction equation
O.[NH2:2][NH2:3].Cl[C:5]1[C:10]([C:11]#[N:12])=[CH:9][C:8]([C:13]#[N:14])=[CH:7][N:6]=1.C(N(CC)CC)C>C(O)C>[C:13]([C:8]1[CH:9]=[C:10]2[C:5](=[N:6][CH:7]=1)[NH:3][N:2]=[C:11]2[NH2:12])#[N:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 109865792-Chloropyridine-3,5-dicarbonitrile

Product 1

HCID 1785103343-amino-1H-Pyrazolo[3,4-b]pyridine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Hydrazine hydrate (55%, 125 mL, 2.20 mmol) was added to a stirred suspension of 2-chloro-3,5-dicyanopyridine (240 mg, 1.47 mmol) and triethylamine (205 μL, 1.47 mmol) in ethanol (3 mL) and the resulting red mixture was heated to 60° C. After 16 h the mixture was cooled and filtered to give the title compound:

Workup

  1. temperatureAfter 16 h the mixture was cooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-fb4f728e33fb4941921077b54130ea1b
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Linked notes

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