Methyl iodide → 3,4-dihydro-6-(3,4-dimethoxyphenyl)-1,3-dimethyl-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinone

HRID 1253071

반응식

HRID 1253071 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]([CH3:17])[C:15](=[O:18])[N:14]([CH3:19])[C:13](=S)[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CI.[CH3:23][C:24]1[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[C:25]=1[NH2:26]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]([CH3:17])[C:15](=[O:18])[N:14]([CH3:19])[C:13](=[N:26][C:25]3[C:27]([CH3:32])=[CH:28][C:29]([CH3:31])=[CH:30][C:24]=3[CH3:23])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 69132,4,6-TrimethylanilineHCID 140964773,4-dihydro-6-(3,4-dimethoxyphenyl)-1,3-dimethyl-4-thioxo-2(1H)-pyrimidinone

생성물 1

HCID 98435333,4-dihydro-6-(3,4-dimethoxyphenyl)-1,3-dimethyl-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinone수율 70.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-1,3-dimethyl-4-thioxo-2(1H)-pyrimidinone (1.51 g) in tetrahydrofuran (150 ml) was added methyl iodide (30 ml) and the mixture was refluxed for 90 minutes. The precipitate was added to 2,4,6-trimethylaniline (6 g) and the mixture was heated at 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)-1,3-dimethyl-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinone (1.44 g); mp 68°-70° C. Thus obtained compound was recrystallized from a mixture of methanol and water (5:1) to give the desired compound as crystals. mp 96°-98° C.

후처리

  1. temperaturethe mixture was refluxed for 90 minutes
  2. temperaturethe mixture was heated at 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

출처 및 근거

ORD 기록
ord-2e3562a4a56349b0842d5f50f7972eb0
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04746664

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