Adenine → 8-trifluoromethyladenine

HRID 1363451Notes

Reaction equation

HRID 1363451 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.S(=O)(=O)(O)O.[F:16][C:17](I)([F:19])[F:18].OO>S([O-])([O-])(=O)=O.[Fe+2].CS(C)=O>[F:16][C:17]([F:19])([F:18])[C:6]1[NH:7][C:8]2[C:4](=[N:3][CH:2]=[N:1][C:9]=2[NH2:10])[N:5]=1

Participants

7

Reactant 4

HCID 190AdenineHCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 16843Trifluoroiodomethane

Product 1

HCID 36354068-trifluoromethyladenineYield 26%

Reagents, catalysts & solvents 2

HCID 24393Ferrous SulfateCatalystHCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
45 °C

Procedure

0.13 g (1.0 mmol) of adenine 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 dimethyl sulfoxide, 2.0 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 1.0 ml of a 3.0 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 8-trifluoromethyladenine (19F-NMR yield: 26%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 8-Trifluoromethyladenine was obtained as a white solid (0.02 g, yield: 10%) by preparative thin-layer 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-990d4dcd55d54ada8095abe368b0dd43
Source dataset
uspto-grants-2011_02
Patent number
US07884202B2

Reaction notes

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