Sodium hydride → 3,4-dihydro-5-methyl-2-[(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]pyrimido[1,6-a]indol-1 (2H)-one

HRID 1657315ノート

反応式

HRID 1657315 の反応式
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[C:11](=[O:15])[NH:12][CH2:13][CH2:14][C:3]=12.[H-].[Na+].Cl[CH2:19][C:20]1[N:21]=[CH:22][N:23]([C:26]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:24]=1[CH3:25]>CN(C)C=O.O>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[C:11](=[O:15])[N:12]([CH2:19][C:20]3[N:21]=[CH:22][N:23]([C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:24]=3[CH3:25])[CH2:13][CH2:14][C:3]=12

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 10465394HCID 10465394、化合物HCID 110469654-(Chloromethyl)-5-methyl-1-trityl-1H-imidazole

生成物 1

HCID 100301163,4-dihydro-5-methyl-2-[(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]pyrimido[1,6-a]indol-1 (2H)-one収率 64.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
5 °C

実験手順

To a solution of 3,4-dihydro-5-methylpyrimido[1,6-a]-indol-1(2H)-one (0.67 g) in N,N-dimethylformamide (8 ml) at 5° C. was added sodium hydride (60% in mineral oil, 0.16 g). The mixture was stirred at 5° C. for 40 minutes and then at room temperature for 15 minutes and again cooled to 5° C. 4-Chloromethyl-5-methyl-1-trityl-1H-imidazole (1.50 g) was added to the solution in small portions over two minutes. After being stirred at 5° C. for 2 hours, the reaction mixture was diluted with chilled water to give precipitates. The precipitates collected were dissolved in dichloromethane. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. Column chromatography (silica gel, 0.5% methanol in chloroform as an eluent) of the residue, followed by recrystallization from toluene-hexane, gave 3,4-dihydro-5-methyl-2-[(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]pyrimido[1,6-a]indol-1 (2H)-one (1.16 g).

後処理

  1. waitat room temperature for 15 minutes
  2. temperatureagain cooled to 5° C
  3. stirringAfter being stirred at 5° C. for 2 hours
  4. customto give
  5. customprecipitates
  6. customThe precipitates collected
  7. dissolutionwere dissolved in dichloromethane
  8. washThe organic layer was washed with water and brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated in vacuo
  11. customColumn chromatography (silica gel, 0.5% methanol in chloroform as an eluent) of the residue, followed by recrystallization from toluene-hexane

出典と根拠

ORDレコード
ord-30cc8a2835e04f4181fc63cbc558c72a
出典データセット
uspto-grants-1993_10
特許番号
US05256780

反応ノート

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