Potassium Carbonate → 2-{[1-Methyl-2-(methyloxy)ethyl]oxy}-8-(methoxy)-9-(tetrahydro-2H-pyran-3-ylmethyl)-9H-purin-6-amine

HRID 1011009

Reaktionsgleichung

Reaktionsgleichung von HRID 1011009
FC(F)(F)C(O)=O.[CH3:8][CH:9]([O:13][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[C:19]([O:23][CH3:24])[NH:20]2)=[C:16]([NH2:25])[N:15]=1)[CH2:10][O:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:37][CH:38]1[CH2:43][CH2:42][CH2:41][O:40][CH2:39]1)(=O)=O>CN(C)C=O.C(OCC)(=O)C>[CH3:8][CH:9]([O:13][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[C:19]([O:23][CH3:24])[N:20]2[CH2:37][CH:38]2[CH2:43][CH2:42][CH2:41][O:40][CH2:39]2)=[C:16]([NH2:25])[N:15]=1)[CH2:10][O:11][CH3:12]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 22402475Tetrahydro-2H-pyran-3-ylmethyl methanesulfonateHCID 178495541HCID 178495541, Verbindung

Produkt 1

HCID 576996982-{[1-Methyl-2-(methyloxy)ethyl]oxy}-8-(methoxy)-9-(tetrahydro-2H-pyran-3-ylmethyl)-9H-purin-6-amineAusbeute 62,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-{[1-methyl-2-(methoxy)ethyl]oxy}-8-(methoxy)-9H-purin-6-amine trifluoroacetic acid salt (500 mg) in dry N,N-dimethylformamide (6.0 ml) at room temperature and under nitrogen was added potassium carbonate (0.75 g) in one go. The reaction was stirred at 60° C. for 1.5 hours. A solution of tetrahydro-2H-pyran-3-ylmethyl methanesulfonate (0.29 g) in dry N,N-dimethylformamide (1.0 ml) was added in one go and the reaction heated at 90° C. for 2 hours. The reaction was cooled to room temperature and then diluted with ethyl acetate (20 ml) and washed with water (10 ml). The organic layer was concentrated in vacuo. The product was purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluant (10-60%) to afford the title compound as a clear viscous oil (300 mg).

Aufarbeitung

  1. temperaturethe reaction heated at 90° C. for 2 hours
  2. temperatureThe reaction was cooled to room temperature
  3. washwashed with water (10 ml)
  4. concentrationThe organic layer was concentrated in vacuo
  5. customThe product was purified by C18 reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-42dacc09ff97452b8fe3689a338675cb
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977344B2

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