HCID 46926326, compound → 5'-amino-5'-deoxyuridine

HRID 985627Notes

Reaction equation

HRID 985627 reaction equation
[N:1]([CH2:4][C@H:5]1[O:9][C@@H:8]([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[C@H:7]([OH:18])[C@@H:6]1[OH:19])=[N+]=[N-]>CO>[NH2:1][CH2:4][C@H:5]1[O:9][C@@H:8]([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[C@H:7]([OH:18])[C@@H:6]1[OH:19]

Participants

3

Reactant 1

HCID 46926326HCID 46926326, compound

Product 1

HCID 114478865'-amino-5'-deoxyuridineYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the 5′-azido-5′-deoxyuridine (2.51 g, 9.33 mmol) obtained as described above in methanol (100 ml) was added palladium-on-carbon Pd/C (10%, about 0.25 g). While bubbling hydrogen (1 atm), the mixture was stirred at room temperature for 2 hours. Then, the reaction mixture obtained was filtered to remove the palladium-on-carbon, the filtrate was evaporated under reduced pressure, and the residue was reprecipitated from methanol-ethanol to give 5′-amino-5′-deoxyuridine (5′-NH2-Urd) (2.22 g, yield 98%) as powders. A white solid.

Workup

  1. customWhile bubbling hydrogen (1 atm)
  2. customThen, the reaction mixture obtained
  3. filtrationwas filtered
  4. customto remove the palladium-on-carbon
  5. customthe filtrate was evaporated under reduced pressure
  6. customthe residue was reprecipitated from methanol-ethanol

Sources & evidence

ORD record
ord-637dd8ca50ec434aa82aad26e7191b08
Source dataset
uspto-grants-2005_03
Patent number
US06872809B2

Reaction notes

Loading…