Pyrazolo[1,5-a]pyriMidine-5-carbonitrile → Pyrazolo[1,5-a]pyrimidine-5-methanamine

HRID 1890572Notes

Reaction equation

HRID 1890572 reaction equation
[N:1]1[N:5]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[N:9][C:4]2=[CH:3][CH:2]=1>N.CO.[Ni]>[N:1]1[N:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH2:11])=[N:9][C:4]2=[CH:3][CH:2]=1

Participants

5

Reactant 1

HCID 23156341Pyrazolo[1,5-a]pyriMidine-5-carbonitrile

Product 1

HCID 67305688Pyrazolo[1,5-a]pyrimidine-5-methanamineYield 94%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

To a solution of pyrazolo[1,5-a]pyrimidine-5-carbonitrile (2-2) (620 mg, 4.31 mmol) in NH3 in MeOH (5 mL) was added Raney Ni (100 mg). The reaction mixture was stirred at room temperature for 3 h under H2. The mixture was filtered, and the filtrate was concentrated to afford the title compound (600 mg). MS (m/z): 149 (M+1)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-323202553a024c9aa4c31514ed975056
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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