Uridine → HCID 46926326, compound

HRID 985626Notes

Reaction equation

HRID 985626 reaction equation
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7]O)[C@@H:4]([OH:5])[C@H:2]1[OH:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N-:37]=[N+:38]=[N-:39].[Li+].C(Br)(Br)(Br)Br>CN(C=O)C.C(Cl)(Cl)Cl.CO.CO>[N:37]([CH2:7][C@H:6]1[O:9][C@@H:1]([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[C@H:2]([OH:3])[C@@H:4]1[OH:5])=[N+:38]=[N-:39]

Participants

8

Reactant 4

HCID 6029UridineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 88163Lithium azide

Product 1

HCID 46926326HCID 46926326, compoundYield 94.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 21584188Chloroform methanolSolvent

Procedure

Uridine (5.5 g, 22.5 mmol), triphenylphosphine (11.8 g, 45.0 mmol) and lithium azide (5.51 g, 112.6 mmol) were dissolved in dried DMF (120 ml). Then, carbon tetrabromide (14.92 g, 45.0 mmol) was added with vigorous stirring and after 2 hours of stirring, about 5 ml of methanol was added to terminate the reaction. The DMF was distilled off under reduced pressure, and the residue was purified by column chromatography (silica gel; chloroform-methanol (30:1 v/v) to give 5′-azido-5′-deoxyuridine (5.40 g, 21.2 mmol, yield 94%). A white solid.

Workup

  1. stirringof stirring
  2. customto terminate
  3. customthe reaction
  4. distillationThe DMF was distilled off under reduced pressure
  5. customthe residue was purified by column chromatography (silica gel

Sources & evidence

ORD record
ord-373b8140222144ec8a6a7d14b0841114
Source dataset
uspto-grants-2005_03
Patent number
US06872809B2

Reaction notes

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