Theophylline → 7-[4-(4-Methylbenzoyl)benzyl]-1,3-dimethylxanthine

HRID 1291421노트

반응식

HRID 1291421 반응식
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[N:5]([CH3:13])[C:3]1=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([C:27]2[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=2)=[O:26])=[CH:23][CH:22]=1>CN(C=O)C.O>[CH3:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([C:27]2[CH:28]=[CH:29][C:30]([CH2:31][N:9]3[C:10]4[C:11](=[O:12])[N:2]([CH3:1])[C:3](=[O:4])[N:5]([CH3:13])[C:6]=4[N:7]=[CH:8]3)=[CH:33][CH:34]=2)=[O:26])=[CH:23][CH:22]=1

참가 물질

6

반응물 3

HCID 2153TheophyllineHCID 11430Potassium CarbonateHCID 108807584-(4-Toluoyl)benzyl bromide

생성물 1

HCID 189191537-[4-(4-Methylbenzoyl)benzyl]-1,3-dimethylxanthine수율 45.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 1,3-dimethylxanthine (99 mg), potassium carbonate (135 mg), 4-(4-methylbenzoyl)benzyl bromide (201 mg) in DMF (10 ml) was stirred at 60° C. for 5 hours. This reaction mixture was poured in water and extracted with ethyl acetate. The extract was washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate =1:5) and recrystallized from ethyl acetate-isopropyl ether to provide the title compound as colorless solid (98 mg).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate =1:5)
  6. customrecrystallized from ethyl acetate-isopropyl ether

출처 및 근거

ORD 기록
ord-e4edcaa068964357a3fa09f747dabab6
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753664

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