Water → Methyl [(2-[5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl]-3-thienyl]oxy]acetate

HRID 48967Notes

Reaction equation

HRID 48967 reaction equation
[OH:1][C:2]1[CH:6]=[CH:5][S: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])[N:18]([CH3:27])[C:17]3=[O:28])[CH:14]=[CH:15][C:10]=2[S:9][N:8]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][C:37]([O:39][CH3:40])=[O:38].O>CN(C)C=O>[CH3:27][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[S:4][CH:5]=[CH:6][C:2]=4[O:1][CH2:36][C:37]([O:39][CH3:40])=[O:38])[C:11]=3[CH:12]=2)[C:17]1=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 135843668HCID 135843668, compound

Product 1

HCID 86584513Methyl [(2-[5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl]-3-thienyl]oxy]acetateYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-[3-(3-hydroxy-2-thienyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil(0.580 g, 1.36 mmol) in dimethylformamide is added potassium carbonate (0.230 g, 1.66 mmol). The resultant mixture is stirred 30 minutes and treated with methyl bromoacetate (0.230 g, 1.50 mmol). The mixture is stirred over a weekend at room temperature and poured into water. Filtration and drying affords the title compound as an off-white solid (0.550 g, 81.4%, mp 73-79° C.) which is identified by NMR spectral analysis.

Workup

  1. filtrationFiltration
  2. customdrying

Sources & evidence

ORD record
ord-c99d940a38ac46a78fb114effce0b787
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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