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

HRID 1818661Notes

Reaction equation

HRID 1818661 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-]>CO.O.[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 91.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a mixture of 5′-azido-2′,5′-dideoxyuridine (5 g, 0.0197 mol) in methanol/water (150 mL, 1:1) was added Pd/C (0.25 g, 10%) under N2 atmosphere and then hydrogenated for 4 h at RT. The reaction mixture was filtered through bed of celite and the filtrate was concentrated under vacuum. The solid obtained was washed with 3% methanol in chloroform which gave the title product (4.1 g, 89%) as an off-white solid.

Workup

  1. filtrationThe reaction mixture was filtered through bed of celite
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe solid obtained
  4. washwas washed with 3% methanol in chloroform which

Sources & evidence

ORD record
ord-7943b5f736ca4423bf954d3a69e4140f
Source dataset
uspto-grants-2009_10
Patent number
US07601702B2

Reaction notes

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