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

HRID 345756Notes

Reaction equation

HRID 345756 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 chloroform 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. customcrystallized from ethanol

Sources & evidence

ORD record
ord-15172931daa34ae89bca5d1637c4ed17
Source dataset
uspto-grants-1991_10
Patent number
US05059590

Reaction notes

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