Potassium Carbonate → N-(4-cyano-phenyl)-2-{4-[6-oxo-1-propyl-7-(2-trimethylsilanyl-ethoxymethyl)-6,7-dihydro-1H-purin-8-yl]-phenoxy}-acetamide

HRID 535994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 535994
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:15]3[C:14](=[O:25])[N:13]([CH2:26][CH2:27][CH3:28])[CH:12]=[N:11][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:36][C:37]([NH:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]#[N:47])=[CH:42][CH:41]=1)=[O:38]>CC(C)=O>[C:46]([C:43]1[CH:42]=[CH:41][C:40]([NH:39][C:37](=[O:38])[CH2:36][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:16]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:23])([CH3:22])[CH3:24])[C:15]4[C:14](=[O:25])[N:13]([CH2:26][CH2:27][CH3:28])[CH:12]=[N:11][C:10]=4[N:9]=3)=[CH:6][CH:7]=2)=[CH:45][CH:44]=1)#[N:47]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 21680152-chloro-N-(4-cyanophenyl)acetamideHCID 1363910238-(4-Hydroxy-phenyl)-1-propyl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one

Produkt 1

HCID 67134763N-(4-cyano-phenyl)-2-{4-[6-oxo-1-propyl-7-(2-trimethylsilanyl-ethoxymethyl)-6,7-dihydro-1H-purin-8-yl]-phenoxy}-acetamideAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 8-(4-hydroxy-phenyl)-1-propyl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.100 g, 0.25 mmol), potassium carbonate (0.052 g, 0.38 mmol), and 2-chloro-N-(4-cyano-phenyl)-acetamide (0.053 g, 0.28 mmol) in acetone (10 ml) was heated at 80° C. for 2 hours. The mixture was cooled to room temperature and filtered through sintered funnel, washed with acetone. The solvent was evaporated and the residue was purified by preparative TLC to obtain pure pale yellow solid of N-(4-cyano-phenyl)-2-{4-[6-oxo-1-propyl-7-(2-trimethylsilanyl-ethoxymethyl)-6,7-dihydro-1H-purin-8-yl]-phenoxy}-acetamide (0.110 g, 79%) as a off white solid.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through sintered funnel
  3. washwashed with acetone
  4. customThe solvent was evaporated
  5. customthe residue was purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-d287a71740784e068a7387cf7a53bbc5
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859566B2

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