Water → 8-(4-Hydroxy-phenyl)-1-propyl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one
Reaktionsgleichung
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:22]3[C:21](=[O:32])[N:20]([CH2:33][CH2:34][CH3:35])[C:19](Cl)=[N:18][C:17]=3[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.O.C([O-])=O.[NH4+]>CN(C=O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:29])([CH3:31])[CH3:30])[C:22]3[C:21](=[O:32])[N:20]([CH2:33][CH2:34][CH3:35])[CH:19]=[N:18][C:17]=3[N:16]=2)=[CH:13][CH:14]=1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a solution of 8-(4-benzyloxy-phenyl)-2-chloro-1-propyl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.25 g, 0.00048 mol) in DMF:water (2.5 ml), 10% Pd/C (0.130 g) and ammonium formate (0.66 g, 0.010 mol) were added and refluxed at 80° C. for 2 hours. The mixture was cooled and filtered through celite bed, solvent was removed and the residue was diluted with water (10 ml), acidified with citric acid and extracted with ethyl acetate (3×10 ml). The organic layer was washed with brine (2×15 ml). It was dried over Na2SO4 and the solvent was removed to obtain pale yellow solid of 8-(4-hydroxy-phenyl)-1-propyl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.153 g, 80%).
Aufarbeitung
- temperatureThe mixture was cooled
- filtrationfiltered through celite bed, solvent
- customwas removed
- additionthe residue was diluted with water (10 ml)
- extractionextracted with ethyl acetate (3×10 ml)
- washThe organic layer was washed with brine (2×15 ml)
- dry with materialIt was dried over Na2SO4
- customthe solvent was removed
Quellen und Nachweise
- ORD-Eintrag
- ord-9a8bc04a139c4cb295e991a49320c4e4
- Quelldatensatz
- uspto-grants-2016_03
- Patentnummer
- US09284316B2
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