5-Methyl-2-nitro-4,5-dihydropyrazolo[1,5-a]pyrazin-6(7H)-one → 2-Amino-5-methyl-4,5-dihydropyrazolo[1,5-a]pyrazin-6(7H)-one

HRID 593124Notes

Reaction equation

HRID 593124 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][N:5]2[N:9]=[C:10]([N+:12]([O-])=O)[CH:11]=[C:4]2[CH2:3]1.[H][H]>C(O)C.[Pd]>[NH2:12][C:10]1[CH:11]=[C:4]2[CH2:3][N:2]([CH3:1])[C:7](=[O:8])[CH2:6][N:5]2[N:9]=1

Participants

5

Reactant 2

HCID 866840315-Methyl-2-nitro-4,5-dihydropyrazolo[1,5-a]pyrazin-6(7H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 866840322-Amino-5-methyl-4,5-dihydropyrazolo[1,5-a]pyrazin-6(7H)-oneYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 313c (450 mg, 2.3 mmol) in ethanol (30 mL) was added Pd/C (10%, 400 mg). The reaction was charged with hydrogen gas (via balloon) and stirred at room temperature for 2 h. After reaction was complete, the mixture was filtered through a plug of CELITE® and the filtrate was concentrated under reduced pressure to afford 313d as a yellow solid (320 mg, 84%), which was used without further purification in the next step. MS-ESI: [M+H]+ 167.1

Workup

  1. customAfter reaction
  2. filtrationthe mixture was filtered through a plug of CELITE®
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-24022a9d32fe4295b61fd40c8caa9b3c
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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