Water → HCID 18394850, compound

HRID 1602738Notes

Reaction equation

HRID 1602738 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@H:13]([OH:14])[C@@H:12]([CH2:15]O)[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.C(Br)(Br)(Br)[Br:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>CN(C=O)C>[CH2:1]([O:8][C@@H:9]1[C@H:13]([OH:14])[C@@H:12]([CH2:15][Br:26])[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

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21856369HCID 21856369, compound

Product 1

HCID 18394850HCID 18394850, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

To a mixture of 2'-O-benzyluridine [Wagner et al. (1974), J. Org. Chem. 39, 24-30] (334 mg 1 mM) carbon tetrabromide (500 mg) and DMF (4 ml) at 20° C. under Argon was added over 5 mins a solution of triphenylphosphine (340 mg) in DMF (2 ml). The mixture was stirred at 20° C. for 2 hrs, poured into water (60 ml) and extracted twice with ethyl acetate. The combined organic extracts were washed with water, dried, and evaporated to an oil. This oil was chromatographed on 20 g of Merck silica gel (Art. 9385). Elution with 5% methanol in toluene gave 2'-O-benzyl-5'-bromo-5'-deoxyuridine (160 mg, 40%).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic extracts were washed with water
  3. customdried
  4. customevaporated to an oil
  5. customThis oil was chromatographed on 20 g of Merck silica gel (Art. 9385)
  6. washElution with 5% methanol in toluene

Sources & evidence

ORD record
ord-de9cbaff02684e9ab62a9ac632593d5e
Source dataset
uspto-grants-1999_11
Patent number
US05985281

Reaction notes

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