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 1646772노트

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HRID 1646772 반응식
[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

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 10465394HCID 10465394, 화합물HCID 110469654-(Chloromethyl)-5-methyl-1-trityl-1H-imidazole

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
5 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-dcbbcfcf9bb64235bc9d3bc0f9112710
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05180728

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