Methyl iodide → FK 664

HRID 621534

Reaction equation

HRID 621534 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]([CH2:17][CH3:18])[C:15](=[O:19])[N:14]([CH3:20])[C:13](=S)[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CI.[CH3:24][C:25]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[C:26]=1[NH2:27]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]([CH2:17][CH3:18])[C:15](=[O:19])[N:14]([CH3:20])[C:13](=[N:27][C:26]3[C:28]([CH3:33])=[CH:29][C:30]([CH3:32])=[CH:31][C:25]=3[CH3:24])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 69132,4,6-TrimethylanilineHCID 212432273,4-dihydro-6-(3,4-dimethoxyphenyl)-1-ethyl-3-methyl-4-thioxo-2(1H)-pyrimidinone

Product 1

HCID 146868FK 664Yield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-1-ethyl-3-methyl-4-thioxo-2(1H)-pyrimidinone (0.59 g) in tetrahydrofuran (50 ml) was added methyl iodide (10 ml) and the mixture was refluxed for 90 minutes. The precipitate was added to 2,4,6-trimethylaniline (2 g) and the mixture was heated to 110°-120° C. for 3 hours. The reaction mixture was washed with a mixture of hexane and diisopropyl ether to remove excess 2,4,6-trimethylaniline. The resulting precipitate was collected by filtration and then dissolved in chloroform. The solution was washed with an aqueous solution of sodium bicarbonate, dried over magnesium sulfate and evaporated under reduced pressure to give crude product, which was purified by silica gel column chromatography to give 3,4-dihydro-6-(3,4-dimethoxyphenyl)-1-ethyl-3-methyl-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinone (0.29 g); mp 57°-61° C. Thus obtained compound was recrystallised from a mixture of ethanol and water (3:1) to give the desired compound as crystals.

Workup

  1. temperaturethe mixture was refluxed for 90 minutes
  2. temperaturethe mixture was heated to 110°-120° C. for 3 hours
  3. washThe reaction mixture was washed with a mixture of hexane and diisopropyl ether
  4. customto remove excess 2,4,6-trimethylaniline
  5. filtrationThe resulting precipitate was collected by filtration
  6. dissolutiondissolved in chloroform
  7. washThe solution was washed with an aqueous solution of sodium bicarbonate
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure
  10. customto give crude product, which
  11. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a74ae822fc4c47c995631f1c20378478
Source dataset
uspto-grants-1989_04
Patent number
US04824851

Linked notes

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