1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(7-Allyl-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)piperazine-1-carboxylic acid tert-butyl ester
Reaktionsgleichung
[CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[N:10]([CH3:14])[C:9](=[O:15])[N:8]([CH3:16])[C:7]=2[N:6]=[C:5]1Cl)[CH:2]=[CH2:3].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].N12CCCN=C1CCCCC2>CN1CCCC1=O>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:5]2[N:4]([CH2:1][CH:2]=[CH2:3])[C:12]3[C:11](=[O:13])[N:10]([CH3:14])[C:9](=[O:15])[N:8]([CH3:16])[C:7]=3[N:6]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 140 °C
Versuchsvorschrift
A mixture of 7-allyl-8-chloro-1,3-dimethyl-3,7-dihydropurine-2,6-dione (1.0 g), piperazine-1-carboxylic acid tert-butyl ester (1.1 g), 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) (0.59 ml), and 1-methylpyrrolidin-2-one (2 ml) were stirred under nitrogen atmosphere in an oil bath at 140° C. for 2 hours. The reaction mixture was extracted with ethyl acetate and water. The organic layer was washed with water followed by saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with 10–20% (20% 2-propanol/ethyl acetate)/hexane to give 1.5 g of the title compound.
Aufarbeitung
- extractionThe reaction mixture was extracted with ethyl acetate and water
- washThe organic layer was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography with 10–20% (20% 2-propanol/ethyl acetate)/hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-c838971beba043dab0973b4dd0a71f71
- Quelldatensatz
- uspto-grants-2006_07
- Patentnummer
- US07074798B2
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