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

HRID 1291415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1291415
[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

Komponenten

6

Edukt 3

HCID 2153TheophyllineHCID 11430Potassium CarbonateHCID 18918912HCID 18918912, Verbindung

Produkt 1

HCID 189190737-[4-(4-Hydroxybenzoyl)benzyl)-1,3-dimethylxanthineAusbeute 109,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d71f9550ab2f4f45a2df1d1bf5e35bd9
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753664

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