4-Nitro-1-(oxetan-3-yl)-1H-imidazole → 1-(Oxetan-3-yl)-1H-imidazol-4-amine

HRID 1022128Notes

Reaction equation

HRID 1022128 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][N:7]([CH:9]2[CH2:12][O:11][CH2:10]2)[CH:8]=1)([O-])=O>[Pd].CO>[O:11]1[CH2:12][CH:9]([N:7]2[CH:8]=[C:4]([NH2:1])[N:5]=[CH:6]2)[CH2:10]1

Participants

4

Reactant 1

HCID 866845194-Nitro-1-(oxetan-3-yl)-1H-imidazole

Product 1

HCID 866845201-(Oxetan-3-yl)-1H-imidazol-4-amineYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 25-mL single-neck round-bottomed flask was purged with nitrogen and charged with 285a (100 mg, 0.6 mmol), 10% palladium on carbon (10% wet, 10 mg) and methanol (10 mL). The flask was evacuated, charged with hydrogen gas (via balloon), and stirred for 1 h at room temperature. The hydrogen was then evacuated and nitrogen was charged to the flask. The catalyst was removed by filtration through a pad of CELITE® and the filtrate was concentrated under reduced pressure to afford 285b (70 mg, 85%). MS-ESI: [M+H]+ 140.3.

Workup

  1. customA 25-mL single-neck round-bottomed flask was purged with nitrogen
  2. customThe flask was evacuated
  3. additioncharged with hydrogen gas (via balloon)
  4. customThe hydrogen was then evacuated
  5. additionnitrogen was charged to the flask
  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-c3c3d85433f24e149de4ccc7922c941a
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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