Dimethyl Sulfate → 3-(4-Choro-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1h, 3h)-pyrimidinedione

HRID 277430Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[NH:10][C:9]2=[O:19])=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1.S(OC)(O[CH3:27])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:17])([F:18])[F:16])[N:10]([CH3:27])[C:9]2=[O:19])=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 3-(4-chloro-2-nitrophenyl)-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (3 g), dimethyl sulfate (1.7 g) and potassium carbonate (1.85 g) in N,N-dimethylformamide (100 ml) was stirred at 55° C. overnight. The resulting mixture was allowed to cool to ambient temperature and filtered through Celite to remove unsoluble precipitate. The filtrate was diluted with a mixed solvent of ethyl acetate and hexane (1:1, 200 ml), washed with brine (×2) and dried over anhydrous sodium sulfate. After removal of the solvent, the residue was solidified. The yellow solid was recrystallized from ethyl acetate and hexane to give desired compound (2.3 g).

Workup

temperatureto cool to ambient temperature
filtrationfiltered through Celite
customto remove unsoluble precipitate
additionThe filtrate was diluted with a mixed solvent of ethyl acetate and hexane (1:1, 200 ml)
washwashed with brine (×2)
dry with materialdried over anhydrous sodium sulfate
customAfter removal of the solvent
customThe yellow solid was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record: ord-465047e65b474da798367bf6c1f29529
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06355799B1

Reaction notes

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