Methyl iodide → 1-Methyl-3-[3-(1-methylpyrrol-2-yl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)uracil

HRID 48963Notes

Reaction equation

HRID 48963 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1[C:11]2[CH:12]=[C:13]([N:16]3[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[NH:18][C:17]3=[O:27])[CH:14]=[CH:15][C:10]=2[S:9][N:8]=1.[C:28](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH3:28][N:18]1[C:19]([C:23]([F:26])([F:25])[F:24])=[CH:20][C:21](=[O:22])[N:16]([C:13]2[CH:14]=[CH:15][C:10]3[S:9][N:8]=[C:7]([C:3]4[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=4)[C:11]=3[CH:12]=2)[C:17]1=[O:27]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 206342623-[3-(1-Methylpyrrol-2-yl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)uracil

Product 1

HCID 206341671-Methyl-3-[3-(1-methylpyrrol-2-yl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)uracilYield 21.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-[3-(1-methylpyrrol-2-yl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)uracil(1.35 g, 3.44 mmol), dry dimethylformamide and potassium carbonate (0.710 g, 5.14 mmol) is added iodomethane (0.730 g, 5.14 mmol). The resultant mixture is stirred overnight at room temperature and poured into ice water. Filtration and drying affords the title compound as a pink foam (0.300 g, 21.4%) which is identified by NMR spectral analysis.

Workup

  1. filtrationFiltration
  2. customdrying

Sources & evidence

ORD record
ord-860be216401c4b5da222ad4032ef4170
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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