Benzyl Bromide → 3-(2-tetrahydrofuranyl)-2'-deoxy-5'-O-benzyl-5-trifluoromethyluridine

HRID 1655489Notes

Reaction equation

HRID 1655489 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[N:6]1[C:19](=[O:20])[C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][N:8]([C@@H:9]2[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[CH2:10]2)[C:7]1=[O:25].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CC(C)=O.[Ag]=O>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[N:6]1[C:19](=[O:20])[C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][N:8]([C@@H:9]2[O:16][C@H:13]([CH2:14][O:15][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@@H:11]([OH:12])[CH2:10]2)[C:7]1=[O:25]

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 14722783HCID 14722783, compound

Product 1

HCID 135184093-(2-tetrahydrofuranyl)-2'-deoxy-5'-O-benzyl-5-trifluoromethyluridine

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 180AcetoneSolvent

Procedure

3.66 Grams of 3-(2-tetrahydrofuranyl)-2'-deoxy-5-trifluoromethyluridine was dissolved in 40 ml of acetone. Thereto were added 5.13 g of benzyl bromide and 5.79 g of silver oxide. The mixture was stirred for 5 hours with refluxing. The reaction mixture was filtered and the filtrate was concentrated. The residue was subjected to silica gel column chromatography (developing solvent : chloroform-methanol=40 : 1). The eluate was recrystallized from dichloromethane-petroleum ether to obtain 0.19 g yield: 4.1%) of 3-(2-tetrahydrofuranyl)-2'-deoxy-5'-O-benzyl-5-trifluoromethyluridine (compound 21) having the melting point of 145° to 147° C.

Workup

  1. temperaturewith refluxing
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe eluate was recrystallized from dichloromethane-petroleum ether

Sources & evidence

ORD record
ord-e7806b0b64cb41ed8e723651edb33716
Source dataset
uspto-grants-1993_10
Patent number
US05250673

Reaction notes

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