1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-Allyl-8-(3,5-dimethylpiperazin-1-yl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione
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].[CH3:18][C@H:19]1[CH2:24][NH:23][CH2:22][C@@H:21]([CH3:25])[NH:20]1.N12CCCN=C1CCCCC2>CN1CCCC1=O.C(OCC)(=O)C.O>[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]1[N:23]1[CH2:22][CH:21]([CH3:25])[NH:20][CH:19]([CH3:18])[CH2:24]1)[CH:2]=[CH2:3]Komponenten
7
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 150 °C
Versuchsvorschrift
A suspension of 7-allyl-8-chloro-1,3-dimethyl-3,7-dihydropurine-2,6-dione (200 mg), cis-2,6-dimethylpiperazine (107 mg), and 1,8-diazabicyclo[5.4.0]undec-7-ene (128 μl) in 1-methyl-2-pyrrolidone (2 ml) was stirred at 150° C. for 50 minutes. The reaction mixture was diluted with ethyl acetate and water, and extracted with ethyl acetate. The aqueous layer was extracted with chloroform, and the combined organic layer was washed with water and dried over magnesium sulfate. The solvent was removed by distillation at reduced pressure to give brown oil. The oil was purified by silica gel column chromatography, and 111 mg of the title compound was obtained from a fraction eluted with methanol-ethyl acetate (1:10).
Aufarbeitung
- extractionextracted with ethyl acetate
- extractionThe aqueous layer was extracted with chloroform
- washthe combined organic layer was washed with water
- dry with materialdried over magnesium sulfate
- customThe solvent was removed by distillation at reduced pressure
- customto give brown oil
- customThe oil was purified by silica gel column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-fa8fc4c9e9274884abd572fa6fada0e9
- Quelldatensatz
- uspto-grants-2006_07
- Patentnummer
- US07074798B2
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