Hydrogen Peroxide → 1,3-Dimethyl-8-(trifluoromethyl)-3,9-dihydro-1H-purine-2,6-dione

HRID 1363461Notes

Reaction equation

[N:1]1([C:12](=[O:13])[C:11]2[NH:10][CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].S(=O)(=O)(O)O.[F:19][C:20](I)([F:22])[F:21].OO>S([O-])([O-])(=O)=O.[Fe+2].CS(C)=O>[F:19][C:20]([F:22])([F:21])[C:9]1[NH:10][C:11]2[C:12](=[O:13])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]=2[N:8]=1

Participants

Conditions

Temperature: 45 °C

Procedure

0.18 g (1.0 mmol) of theophylline 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-trifluoromethyltheophylline (19F-NMR yield: 48%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 8-Trifluoromethyltheophylline was obtained as a white solid (0.086 g, yield: 35%) 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-1f75b89cae444282b3a8e77927995e0a
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884202B2

Reaction notes

Loading…