2-Azido-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1H-benzimidazole → 2-Amino-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1H-benzimidazole

HRID 1985816Notes

Reaction equation

HRID 1985816 reaction equation
[N:1]([C:4]1[N:8]([C@@H:9]2[O:21][C@H:20]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]2[O:11][C:12](=[O:14])[CH3:13])[C:7]2[CH:27]=[CH:28][CH:29]=[CH:30][C:6]=2[N:5]=1)=[N+]=[N-]>CO.[C].[Pd]>[NH2:1][C:4]1[N:8]([C@@H:9]2[O:21][C@H:20]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]2[O:11][C:12](=[O:14])[CH3:13])[C:7]2[CH:27]=[CH:28][CH:29]=[CH:30][C:6]=2[N:5]=1

Participants

4

Reactant 1

HCID 866182782-Azido-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1H-benzimidazole

Product 1

HCID 688410382-Amino-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1H-benzimidazoleYield 103.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-Azido-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-benzimidazole (100 mg) was dissolved in methanol (2 mL). To the solution was added a catalytic amount of 10% palladium-carbon powder, and the mixture was stirred at room temperature under a hydrogen atmosphere for 1 hour. The insoluble material was removed by filtration, and the solvent of filtrate was removed under reduced pressure to give the title compound (97 mg).

Workup

  1. customThe insoluble material was removed by filtration
  2. customthe solvent of filtrate was removed under reduced pressure

Sources & evidence

ORD record
ord-73cb82c0a8ce43b08e8ff1e807522535
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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