Uridine, 5'-azido-2',5'-dideoxy- → Uridine, 5'-amino-2',5'-dideoxy-

HRID 1974222Notes

Reaction equation

HRID 1974222 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])[CH2:7][C@@H:6]1[OH:18])=[N+]=[N-]>C(O)C.[C].[Pd]>[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])[CH2:7][C@@H:6]1[OH:18]

Participants

4

Reactant 1

HCID 451825Uridine, 5'-azido-2',5'-dideoxy-

Product 1

HCID 451827Uridine, 5'-amino-2',5'-dideoxy-Yield 56%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

5'-azido-2',5'-dideoxyuridine (258 mg, 1 mmole) is dissolved in 50 ml of ethanol and 50 mg of 10% palladium carbon catalyst added. The suspension is maintained at atmospheric pressure in a hydrogenation apparatus for 2.5 hours before filtering through Celite. The solvent is removed in vacuo, the residue dissolved in water and applied to a column of Dowex 50 (H+) resin. After washing the column with 100 ml of water, the 5'-amino-2',5'-dideoxyuridine is eluted with 100 ml of 1M NH4OH. The solution is evaporated to dryness and the residue crystallized from ethanol-ether to provide the desired product, (127 mg, 56%).

Workup

  1. temperatureThe suspension is maintained at atmospheric pressure in a hydrogenation apparatus for 2.5 hours
  2. filtrationbefore filtering through Celite
  3. customThe solvent is removed in vacuo
  4. dissolutionthe residue dissolved in water
  5. washAfter washing the column with 100 ml of water
  6. washthe 5'-amino-2',5'-dideoxyuridine is eluted with 100 ml of 1M NH4OH
  7. customThe solution is evaporated to dryness
  8. customthe residue crystallized from ethanol-ether

Sources & evidence

ORD record
ord-becefd3557f04f48a757740ea9d19933
Source dataset
uspto-grants-1976_12
Patent number
US04000260

Reaction notes

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