Hydrogen Peroxide → 8-(trifluoromethyl)-9H-purin-6-ol

HRID 1363457Notes

Reaction equation

[NH:1]1[C:9](=[O:10])[C:8]2[NH:7][CH:6]=[N:5][C:4]=2[N:3]=[CH:2]1.S(=O)(=O)(O)O.[F:16][C:17](I)([F:19])[F:18].OO>[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].CS(C)=O>[F:16][C:17]([F:19])([F:18])[C:6]1[NH:7][C:8]2[C:9](=[O:10])[NH:1][CH:2]=[N:3][C:4]=2[N:5]=1

Participants

Conditions

Temperature: 65 °C

Procedure

0.14 g (1.0 mmol) of hypoxanthine and 0.058 g (0.3 mmol) of ferrocene were 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 of dimethyl sulfoxide solution of trifluoromethyl iodide and 0.2 ml of a 30% hydrogen peroxide aqueous solution. The mixture was stirred at 60 to 70° C. for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 8-trifluoromethylhypoxanthine (19F-NMR yield: 24%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 8-Trifluoromethylhypoxanthine was obtained (0.026 g, yield: 13%) by column chromatography.

Workup

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

Sources & evidence

ORD record: ord-478ea7a6e6ab4b2880bc54caa8af2c9b
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884202B2

Reaction notes

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