Potassium Carbonate → N2-(2-Cyclopropylethyl)-8-(methyloxy)-9-(tetrahydro-2H-pyran-3-ylmethyl)-9H-purine-2,6-diamine

HRID 1011047Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1011047
FC(F)(F)C(O)=O.[CH:8]1([CH2:11][CH2:12][NH:13][C:14]2[N:22]=[C:21]3[C:17]([N:18]=[C:19]([O:23][CH3:24])[NH:20]3)=[C:16]([NH2:25])[N:15]=2)[CH2:10][CH2:9]1.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>[CH:8]1([CH2:11][CH2:12][NH:13][C:14]2[N:22]=[C:21]3[C:17]([N:18]=[C:19]([O:23][CH3:24])[N:20]3[CH2:37][CH:38]3[CH2:43][CH2:42][CH2:41][O:40][CH2:39]3)=[C:16]([NH2:25])[N:15]=2)[CH2:10][CH2:9]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 22402475Tetrahydro-2H-pyran-3-ylmethyl methanesulfonateHCID 178493988N2-(2-Cyclopropylethyl)-8-(methoxy)-9H-Purine-2,6-diamine trifluoroacetate

Produkt 1

HCID 57699575N2-(2-Cyclopropylethyl)-8-(methyloxy)-9-(tetrahydro-2H-pyran-3-ylmethyl)-9H-purine-2,6-diamineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of N2-(2-cyclopropylethyl)-8-(methoxy)-9H-purine-2,6-diamine trifluoroacetate (400 mg) in N,N-dimethylformamide (6.90 ml) at room temperature was added potassium carbonate (610 mg) and the reaction stirred at 60° C. for 90 minutes. The reaction mixture was cooled to room temperature and tetrahydro-2H-pyran-3-ylmethyl methanesulfonate (236 mg) was added. Stirring was continued at 50° C. for 20 hours. The reaction temperature was increased to 90° C. and stirring continued. The reaction was cooled and taken up in ethyl acetate (50 ml) and washed with water (2×50 ml). The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo to give an orange oil. The product was purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluant (10-50%) to afford the title compound as a colourless oil (198 mg, 88% pure).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringStirring
  3. waitwas continued at 50° C. for 20 hours
  4. temperatureThe reaction temperature was increased to 90° C.
  5. stirringstirring
  6. temperatureThe reaction was cooled
  7. washwashed with water (2×50 ml)
  8. customThe organic layer was separated
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto give an orange oil
  13. customThe product was purified by C18 reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-be4bc315c52b41e5bcdb534c7b347c54
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977344B2

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