Methyl iodide → {{5-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl}oxy}acetonitrile

HRID 277390Notes

Reaction equation

HRID 277390 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][C:4](=[O:12])[N:3]1[C:13]1[CH:14]=[CH:15][C:16]2[S:20][N:19]=[C:18]([O:21][CH2:22][C:23]#[N:24])[C:17]=2[CH:25]=1.[C:26](=O)([O-])[O-].[K+].[K+].IC.C(Cl)Cl>CN(C)C=O.C(OCC)(=O)C>[CH3:26][N:7]1[C:6]([C:8]([F:9])([F:11])[F:10])=[CH:5][C:4](=[O:12])[N:3]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([O:21][CH2:22][C:23]#[N:24])[C:17]=3[CH:25]=2)[C:2]1=[O:1]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 15477614{{5-[3,6-Dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl}oxy}acetonitrile

Product 1

HCID 15906562{{5-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl}oxy}acetonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of {{5-[3,6-dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl}oxy}acetonitrile (2.63 g, 7.15 mmol) and potassium carbonate (1.97 g, 14.3 mmol) in N,N-dimethylformamide is stirred for 30 minutes, treated with iodomethane (2.03 g, 14.3 mmol), stirred overnight at room temperature, and poured into an ice-water mixture. The resultant aqueous mixture is filtered to obtain a solid. The solid is dissolved in ethyl acetate and the resultant solution is washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a brown solid. Column chromatography of the solid using silica gel and methylene chloride affords a yellow solid. The yellow solid is recrystallized from a methylene chloride/hexanes solution to give the title product as an off-white solid, mp 265-266° C.

Workup

  1. stirringstirred overnight at room temperature
  2. filtrationThe resultant aqueous mixture is filtered
  3. customto obtain a solid
  4. washthe resultant solution is washed sequentially with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a brown solid
  8. customaffords a yellow solid
  9. customThe yellow solid is recrystallized from a methylene chloride/hexanes solution

Sources & evidence

ORD record
ord-9605f85bdef24ecbb64afb1707d0ad62
Source dataset
uspto-grants-2002_03
Patent number
US06355796B1

Reaction notes

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