Hydrogen Peroxide → 5-Ethynyl-1-pentofuranosyl-1H-imidazole-4-carboximidic acid

HRID 893706Notes

Reaction equation

HRID 893706 reaction equation
[C:1]([C:3]1[N:7]([C@@H:8]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:11]([OH:12])[C@H:9]2[OH:10])[CH:6]=[N:5][C:4]=1[C:17]#[N:18])#[CH:2].[OH:19]O>N.CO>[C:1]([C:3]1[N:7]([C@@H:8]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:11]([OH:12])[C@H:9]2[OH:10])[CH:6]=[N:5][C:4]=1[C:17]([NH2:18])=[O:19])#[CH:2]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 11043123HCID 11043123, compound

Product 1

HCID 4531805-Ethynyl-1-pentofuranosyl-1H-imidazole-4-carboximidic acid

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

To a solution of 127 mg (0.51 mmol) of 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carbonitrile dissolved in 6 ml of a solvent mixture of aqueous ammonia and methanol (1:1) was added 0.5 ml of hydrogen peroxide, and the reaction was carried out with stirring at room temperature for 45 minutes. After the reaction, the solvent was evaporated, and the residue was adsorbed onto a silica gel column and eluted with a 5 - 10% ethanolchloroform solvent mixture, and crystallized from ethanol to obtain white crystals of 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide.

Workup

  1. customAfter the reaction
  2. customthe solvent was evaporated
  3. washeluted with a 5 - 10% ethanolchloroform solvent mixture
  4. customcrystallized from ethanol

Sources & evidence

ORD record
ord-1a8a7ec297a44b34a09c6d4c8223575f
Source dataset
uspto-grants-1992_06
Patent number
US05126361

Reaction notes

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