Methyl iodide → HCID 18549204, compound

HRID 1266194Notes

Reaction equation

HRID 1266194 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[CH2:9]([N:12]1[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]=[C:13]1[SH:23])[CH:10]=[CH2:11]>CN(C=O)C>[CH2:9]([N:12]1[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:20])([F:22])[F:21])[N:14]=[C:13]1[S:23][CH3:1])[CH:10]=[CH2:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178456615HCID 178456615, compound

Product 1

HCID 18549204HCID 18549204, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Next, potassium carbonate (22.5 g, 163 mmol) and methyl iodide (10.2 ml, 164 mmol) were added to DMF (110 ml) solution of 3-allyl-2-mercapto-6-trifluoromethyl-4(3H)-pyrimidinone (32.1 g, 136 mmol) with stirring under ice-cooling, followed by stirring for 23 hours while gradually returning to room temperature. After completion of the reaction, the reaction solution was concentrated under a reduced pressure, saturated brine (100 ml), water (100 ml) and ethyl acetate (300 ml) were added to the thus obtained residue to separate the organic layer and then the aqueous layer was extracted with ethyl acetate (100 ml×2). The organic layers were combined, washed with saturated brine (50 ml×2) and then dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the resulting filtrate was concentrated under a reduced pressure. The thus obtained crude product was purified, by a silica gel column chromatography (hexane˜hexane:ethyl acetate=9:1) to obtain white solid of 3-allyl-2-methylthio-6-trifluoromethyl-4(3H)-pyrimidinone (26.9 g, 79%).

Workup

  1. temperaturecooling
  2. stirringby stirring for 23 hours
  3. customwhile gradually returning to room temperature
  4. customAfter completion of the reaction
  5. concentrationthe reaction solution was concentrated under a reduced pressure, saturated brine (100 ml), water (100 ml) and ethyl acetate (300 ml)
  6. additionwere added to the thus obtained residue
  7. customto separate the organic layer
  8. extractionthe aqueous layer was extracted with ethyl acetate (100 ml×2)
  9. washwashed with saturated brine (50 ml×2)
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe drying agent was removed by filtration
  12. concentrationthe resulting filtrate was concentrated under a reduced pressure
  13. customThe thus obtained crude product
  14. customwas purified, by a silica gel column chromatography (hexane˜hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-768d0bfd45d24349872aa383b7b9b600
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

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