2-Nitro-5-(oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine → 5-(Oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amine

HRID 407807Notes

Reaction equation

HRID 407807 reaction equation
[N+:1]([C:4]1[CH:16]=[C:7]2[CH2:8][N:9]([CH:12]3[CH2:15][O:14][CH2:13]3)[CH2:10][CH2:11][N:6]2[N:5]=1)([O-])=O>[Pd].CO>[O:14]1[CH2:15][CH:12]([N:9]2[CH2:10][CH2:11][N:6]3[N:5]=[C:4]([NH2:1])[CH:16]=[C:7]3[CH2:8]2)[CH2:13]1

Participants

4

Reactant 1

HCID 667429562-Nitro-5-(oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

Product 1

HCID 667430935-(Oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amineYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 50-mL single-neck round-bottomed flask was purged with nitrogen and charged with 155a (0.20 g, 0.89 mmol), 10% palladium on carbon (50% wet, 89 mg), and methanol (10 mL). The mixture was evacuated, charged with hydrogen gas, and stirred for 2 h at room temperature. The hydrogen was then evacuated and nitrogen was charged into the bottle. The catalyst was removed by filtration through a pad of CELITE® and the filtrate was concentrated under reduced pressure to afford 155b (140 mg, 81%). MS: [M+H]+ 195.1

Workup

  1. customA 50-mL single-neck round-bottomed flask was purged with nitrogen
  2. customThe mixture was evacuated
  3. additioncharged with hydrogen gas
  4. customThe hydrogen was then evacuated
  5. additionnitrogen was charged into the bottle
  6. customThe catalyst was removed by filtration through a pad of CELITE®
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c30684f63954437fa3049667e3d7ef65
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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