5-Methyl-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-A]pyrazine → 5-methyl-4H,5H,6H,7H-pyrazolo[1,5-a]pyrazin-2-amine

HRID 1431175Notes

Reaction equation

HRID 1431175 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]2[N:8]=[C:9]([N+:11]([O-])=O)[CH:10]=[C:4]2[CH2:3]1>C(O)C.[Pd]>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]2[N:8]=[C:9]([NH2:11])[CH:10]=[C:4]2[CH2:3]1

Participants

4

Reactant 1

HCID 580440245-Methyl-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-A]pyrazine

Product 1

HCID 580439335-methyl-4H,5H,6H,7H-pyrazolo[1,5-a]pyrazin-2-amineYield 127.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-methyl-2-nitro-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazine (67 mg, 0.37 mmol) in ethanol (15 mL) was treated with palladium on carbon (10%, 20 mg) and flushed with argon. The resulting mixture was stirred under a hydrogen (1 atm) overnight. The reaction mixture was filtered through a celite pad, and the pad washed with ethanol. The filtrate was concentrated in vacuo to give 5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amine (72 mg, quantitative) as a light yellow oil.

Workup

  1. customflushed with argon
  2. filtrationThe reaction mixture was filtered through a celite pad
  3. washthe pad washed with ethanol
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-db61346908f74e6a908586e8bd6ea927
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

Loading…