Sodium Azide → HCID 18394851, compound

HRID 1602739Notes

Reaction equation

HRID 1602739 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@H:13]([OH:14])[C@@H:12]([CH2:15]Br)[O:11][C@H:10]1[N:17]1[CH:24]=[CH:23][C:21](=[O:22])[NH:20][C:18]1=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C>[N:25]([CH2:15][C@H:12]1[O:11][C@@H:10]([N:17]2[CH:24]=[CH:23][C:21](=[O:22])[NH:20][C:18]2=[O:19])[C@H:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@@H:13]1[OH:14])=[N+:26]=[N-:27]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 18394850HCID 18394850, compound

Product 1

HCID 18394851HCID 18394851, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2'-O-Benzyl-5'-bromo-5'-deoxyuridine (4.3 g) was dissolved in DMF (86 ml) and sodium azide (7 g) added. The mixture was stirred and heated at 60° C. for 45 mins. After cooling and decanting from unreacted sodium azide the DMF was evaporated to dryness. The residue was dissolved in ethyl acetate and washed twice with water, dried and evaporated to dryness. The residue was chromatographed on Merck silica gel (Art. 9385). Elution with 10% methanol in toluene gave 1.5 g of pure 5'-azido-2'-O-benzyl-5'-deoxyuridine.

Workup

  1. temperatureAfter cooling
  2. customdecanting from unreacted sodium azide the DMF
  3. customwas evaporated to dryness
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed twice with water
  6. customdried
  7. customevaporated to dryness
  8. customThe residue was chromatographed on Merck silica gel (Art. 9385)
  9. washElution with 10% methanol in toluene

Sources & evidence

ORD record
ord-fb93aeb8afe2471296e65bbd233a81f7
Source dataset
uspto-grants-1999_11
Patent number
US05985281

Reaction notes

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