Potassium Carbonate → 7-[4-(4-Chlorobenzoyl)benzyl]-3-methyl-1-propylxanthine

HRID 1291410

Reaktionsgleichung

Reaktionsgleichung von HRID 1291410
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([C:18](=[O:26])[C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=4)=[CH:14][CH:13]=3)[C:6]=2[C:5](=[O:27])[NH:4][C:3]1=[O:28].C(=O)([O-])[O-].[K+].[K+].[CH2:35](I)[CH2:36][CH3:37]>CN(C=O)C.O>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([C:15]2[CH:14]=[CH:13][C:12]([CH2:11][N:7]3[C:6]4[C:5](=[O:27])[N:4]([CH2:35][CH2:36][CH3:37])[C:3](=[O:28])[N:2]([CH3:1])[C:10]=4[N:9]=[CH:8]3)=[CH:17][CH:16]=2)=[O:26])=[CH:20][CH:21]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 189188013-Methyl-7-[4-(4-chlorobenzoyl)benzyl]xanthine

Produkt 1

HCID 189190077-[4-(4-Chlorobenzoyl)benzyl]-3-methyl-1-propylxanthineAusbeute 48,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-methyl-7-[4-(4-chlorobenzoyl)benzyl]xanthine (657 mg), potassium carbonate (242 mg) and propyl iodide (427 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 =1:1) and recrystallized from ethyl acetate to provide the title compound as colorless solid (352 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 =1:1)
  6. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4988ba6bbf1e484989f3db1b12a121fc
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753664

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