Methyl iodide → HCID 18549213, compound

HRID 1266191Notes

Reaction equation

HRID 1266191 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[CH2:7]([N:9]1[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]=[C:10]1[SH:20])[CH3:8].CI>CN(C=O)C>[CH2:7]([N:9]1[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[N:11]=[C:10]1[S:20][CH3:1])[CH3:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178462983HCID 178462983, compound

Product 1

HCID 18549213HCID 18549213, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Next, potassium carbonate (8.15 g, 59.0 mmol) was added to DMF (100 ml) solution of 3-ethyl-2-mercapto-6-trifluoromethyl-4(3H)-pyrimidinone (11.0 g, 49.0 mmol), methyl iodide (3.68 ml, 59.0 mmol) was added with stirring under ice-cooling, followed by stirring for 4 hours while gradually returning to room temperature. After completion of the reaction, the reaction solution was concentrated under a reduced pressure, water (100 ml) and ethyl acetate (100 ml) were added to the thus obtained residue to separate the organic layer, and then the aqueous layer was extracted with ethyl acetate (50 ml×3). The organic layers were combined, washed with water (100 ml×3) and saturated brine (300 ml) and then dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and then the resulting filtrate was concentrated under a reduced pressure to obtain 3-ethyl-2-methylthio-6-trifluoromethyl-4(3H)-pyrimidinone (11.0 g, 94%).

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringby stirring for 4 hours
  4. customwhile gradually returning to room temperature
  5. customAfter completion of the reaction
  6. concentrationthe reaction solution was concentrated under a reduced pressure, water (100 ml) and ethyl acetate (100 ml)
  7. additionwere added to the thus obtained residue
  8. customto separate the organic layer
  9. extractionthe aqueous layer was extracted with ethyl acetate (50 ml×3)
  10. washwashed with water (100 ml×3) and saturated brine (300 ml)
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe drying agent was removed by filtration
  13. concentrationthe resulting filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-a048c0b4e8b64bc49aa20e6196be5539
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

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