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

HRID 65160

反応式

HRID 65160 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-539b917369d54db2904995e6563294db
出典データセット
uspto-grants-1986_09
特許番号
US04612376

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