Methyl iodide → HCID 68695751, compound

HRID 2243224Notes

Reaction equation

HRID 2243224 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH3:7][CH:8]1[CH:12]([CH3:13])[O:11][C:10]([C:14]2([C:20]3[CH:21]=[C:22]([S:26][C:27]4[CH:32]=[CH:31][C:30]([N:33]5[C:37](=O)[NH:36][C:35]([CH3:39])=[N:34]5)=[CH:29][CH:28]=4)[CH:23]=[CH:24][CH:25]=3)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[N:9]1.CI>CN(C)C=O>[CH3:7][CH:8]1[CH:12]([CH3:13])[O:11][C:10]([C:14]2([C:20]3[CH:21]=[C:22]([S:26][C:27]4[CH:28]=[CH:29][C:30]([N:33]5[C:1](=[O:4])[N:36]([CH3:37])[C:35]([CH3:39])=[N:34]5)=[CH:31][CH:32]=4)[CH:23]=[CH:24][CH:25]=3)[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)=[N:9]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 136353894HCID 136353894, compound

Product 1

HCID 68695751HCID 68695751, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Solid potassium carbonate (4.5 mmol) is added to a solution of 2-[4-({3-[4-(4,5-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)tetrahydro-2H-pyran-4-yl]phenyl}thio)phenyl]-5-methyl-2,4-dihydro-3H-1,2,4-traizol-3-one (1.0 mmol) (example 21) in dry dimethylformamide. The reaction mixture is stirred a room temperature for about 15 minutes. Methyl iodide (3.0 mmol) is added and the reaction mixture is heated at about 100° C. for about 12 hours. The solvent is evaporated under vacuum, water is added and the reaction mixture is extracted with ethyl acetate. The organic layer is washed with water, dried over anhydrous sodium sulphate, filtered and the solvent is evaporated to afford the residue. Column chromatography of the residue over silica gel affords the title compound.

Workup

  1. temperaturethe reaction mixture is heated at about 100° C. for about 12 hours
  2. customThe solvent is evaporated under vacuum, water
  3. additionis added
  4. extractionthe reaction mixture is extracted with ethyl acetate
  5. washThe organic layer is washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customthe solvent is evaporated
  9. customto afford the residue

Sources & evidence

ORD record
ord-c89e43c06ff246ab9e3e46f0d87c5c08
Source dataset
uspto-grants-2010_03
Patent number
US07674811B2

Reaction notes

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