Methyl iodide → HCID 12993858, compound

HRID 1835051Notes

Reaction equation

HRID 1835051 reaction equation
[CH3:1][C:2]([C:5](=[N:10][NH:11][C:12](=[O:34])[C:13]1[CH:18]=[C:17]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]2=[O:31])[C:16]([F:32])=[CH:15][C:14]=1[Cl:33])[C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:4])[CH3:3].CI.[C:37](=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:4][C:2]([C:5](=[N:10][N:11]([CH3:37])[C:12](=[O:34])[C:13]1[CH:18]=[C:17]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]2=[O:31])[C:16]([F:32])=[CH:15][C:14]=1[Cl:33])[C:6]([CH3:7])([CH3:8])[CH3:9])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12993857HCID 12993857, compound

Product 1

HCID 12993858HCID 12993858, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixed solution of 2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl)-4-fluoro-benzoic acid, 2-[1-(1,1-dimethylethyl)-2,2-dimethylpropylidene]hydrazide (0.48 g), excess of methyl iodide and potassium carbonate (0.132 g) in acetonitrile (20 ml) was heated at reflux temperature overnight. The mixture was allowed to cool to ambient temperature and partitioned between ethyl acetate and brine. The organic phase was washed with brine (×3) and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluted with a mixed solvent of ethyl acetate and hexane (1:4 to 1:2) to give the titled compound (0.25 g) along with its, 2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl)-4-fluoro-benzoic acid, 2-[1-(1,1-dimethylethyl)-2,2-dimethylpropylidene]-1-methylhydrazide (0.1 g, Compound No. 6-8)

Workup

  1. temperatureat reflux temperature overnight
  2. custompartitioned between ethyl acetate and brine
  3. washThe organic phase was washed with brine (×3)
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel
  7. washeluted with a mixed solvent of ethyl acetate and hexane (1:4 to 1:2)

Sources & evidence

ORD record
ord-d6d78ed4bfa34fceac563908926dfd94
Source dataset
uspto-grants-2004_08
Patent number
US06770597B2

Reaction notes

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