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

HRID 1291415노트

반응식

HRID 1291415 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+].[O:20]([C:28]1[CH:43]=[CH:42][C:31]([C:32]([C:34]2[CH:41]=[CH:40][C:37]([CH2:38]Br)=[CH:36][CH:35]=2)=[O:33])=[CH:30][CH:29]=1)[Si](C(C)(C)C)(C)C>CN(C=O)C.O>[OH:20][C:28]1[CH:29]=[CH:30][C:31]([C:32]([C:34]2[CH:41]=[CH:40][C:37]([CH2:38][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:36][CH:35]=2)=[O:33])=[CH:42][CH:43]=1

참가 물질

6

반응물 3

HCID 2153TheophyllineHCID 11430Potassium CarbonateHCID 18918912HCID 18918912, 화합물

생성물 1

HCID 189190737-[4-(4-Hydroxybenzoyl)benzyl)-1,3-dimethylxanthine수율 109.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 1,3-dimethylxanthine (742 mg), potassium carbonate (569 mg) and 4-(4-t-butyldimethylsiloxybenzoyl)benzyl bromide (2292 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 =1:3) and recrystallized from chloroform-isopropyl ether to provide the title compound as colorless solid (1763 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 =1:3)
  6. customrecrystallized from chloroform-isopropyl ether

출처 및 근거

ORD 기록
ord-d71f9550ab2f4f45a2df1d1bf5e35bd9
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753664

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