Hydrogen Peroxide → HCID 57693287, compound

HRID 1363442Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[N:14]([CH3:15])[C:13](=[O:16])[N:12]([CH3:17])[C:11](=[O:18])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(=O)(=O)(O)O.[F:24][C:25](I)([F:27])[F:26].OO>S([O-])([O-])(=O)=O.[Fe+2].CS(C)=O>[C:1]([O:5][C:6]([NH:8][C:9]1[N:14]([CH3:15])[C:13](=[O:16])[N:12]([CH3:17])[C:11](=[O:18])[C:10]=1[C:25]([F:27])([F:26])[F:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

0.26 g (1.0 mmol) of 6-tert-butoxycarbonylamino-1,3-dimethyluracil 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 6-tert-butoxycarbonylamino-1,3-dimethyl-5-trifluoromethyluracil (19F-NMR yield: 95%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 6-tert-Butoxycarbonylamino-1,3-dimethyl-5-trifluoromethyluracil was obtained as a white solid (0.30 g, yield: 93%) 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-acf95923a03c4575a335a61f48a735ff
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884202B2

Reaction notes

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