Hydrogen Peroxide → Trifluridine

HRID 1363445Notes

Reaction equation

HRID 1363445 reaction equation
[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.S(=O)(=O)(O)O.[F:22][C:23](I)([F:25])[F:24].OO>S([O-])([O-])(=O)=O.[Fe+2].CS(C)=O>[F:22][C:23]([F:25])([F:24])[C:15]1[C:13](=[O:14])[NH:12][C:10](=[O:11])[N:9]([CH:16]=1)[C@@H:1]1[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 13712DeoxyuridineHCID 16843Trifluoroiodomethane

Product 1

HCID 6256TrifluridineYield 85%

Reagents, catalysts & solvents 2

HCID 24393Ferrous SulfateCatalystHCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
45 °C

Procedure

0.23 g (1.0 mmol) of 2′-deoxyuridine was weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 2.0 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 1.0 ml of a 2.1 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.2 ml of a 30% hydrogen peroxide aqueous solution and 0.3 ml of a 1.0 mol/l aqueous solution of iron (II) sulfate. The mixture was stirred at 40 to 50° C. for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyl-2′-deoxyuridine (19F-NMR yield: 85%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 5-Trifluoromethyl-2′-deoxyuridine was obtained as a white solid (0.17 g, yield: 58%) by column chromatography.

Workup

  1. customplaced in a 50 ml two-neck flask
  2. customequipped with a magnetic rotor
  3. additionThe following materials were added
  4. temperaturethe resulting solution was cooled to room temperature

Sources & evidence

ORD record
ord-e455fd15a0244ff3ab57923ceedd8d1e
Source dataset
uspto-grants-2011_02
Patent number
US07884202B2

Reaction notes

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