Benzyl Bromide → Uridine, 2'-deoxy-5-fluoro-3'-O-(phenylmethyl)-

HRID 703560Notes

Reaction equation

HRID 703560 reaction equation
[C:1]([O:20][CH2:21][C@H:22]1[O:26][C@@H:25]([N:27]2[CH:34]=[C:33]([F:35])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:24][C@@H:23]1[OH:36])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(Br)C1C=CC=CC=1.[OH-].[K+]>O1CCOCC1>[CH2:1]([O:20][C@@H:21]1[C@@H:22]([CH2:23][OH:36])[O:26][C@@H:25]([N:27]2[CH:34]=[C:33]([F:35])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:24]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 108387042'-deoxy-5'-O-trityl-5-fluorouridine

Product 1

HCID 10664574Uridine, 2'-deoxy-5-fluoro-3'-O-(phenylmethyl)-Yield 72.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In 50 ml of dioxane was dissolved 10 g of 2'-deoxy-5'-O-trityl-5-fluorouridine. To the solution were added 2.9 ml of benzyl bromide and 14.6 g of particles of potassium hydroxide. The mixture was stirred at room temperature for 1 hour. The solvent was distilled off and the residue was dissolved in 80 ml of a 80% solution of acetic acid to undergo reaction at 50° to 60° C. for 2 hours. The reaction mixture was cooled with ice for 1 hour, the trityl alcohol was separated by filtration and the mother liquor was concentrated. To the concentrate was added ethanol and the mixture was stirred. The crystals precipitated were separated by filtration and dried, affording 5.0 g of the title compound in a yield of 72

Workup

  1. distillationThe solvent was distilled off
  2. dissolutionthe residue was dissolved in 80 ml of a 80% solution of acetic acid
  3. customreaction at 50° to 60° C. for 2 hours
  4. temperatureThe reaction mixture was cooled with ice for 1 hour
  5. customthe trityl alcohol was separated by filtration
  6. concentrationthe mother liquor was concentrated
  7. additionTo the concentrate was added ethanol
  8. stirringthe mixture was stirred
  9. customThe crystals precipitated
  10. customwere separated by filtration
  11. customdried

Sources & evidence

ORD record
ord-d96685647abd4802b78145b91fac0fc4
Source dataset
uspto-grants-1991_01
Patent number
US04983609

Reaction notes

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