Potassium Carbonate → N2-Butyl-8-(methoxy)-9-(tetrahydro-3-furanylmethyl)-9H-Purine-2,6-diamine

HRID 1011053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1011053
FC(F)(F)C(O)=O.[CH2:8]([NH:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:36][CH:37]1[CH2:41][CH2:40][O:39][CH2:38]1)(=O)=O.ClC1N=C2C(N=CN2CC2CCOCC2)=C(Cl)N=1>CN(C)C=O.C(OCC)(=O)C>[CH2:8]([NH:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:36][CH:37]2[CH2:41][CH2:40][O:39][CH2:38]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 22273010(Tetrahydrofuran-3-yl)methyl methanesulfonateHCID 576997032,6-Dichloro-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purineHCID 178448879HCID 178448879, Verbindung

Produkt 1

HCID 57699650N2-Butyl-8-(methoxy)-9-(tetrahydro-3-furanylmethyl)-9H-Purine-2,6-diamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of N2-butyl-8-methoxy-9H-purine-2,6-diamine trifluoroacetic acid salt (4.60 g) in dry N,N-dimethylformamide (55 ml) at room temperature and under was added potassium carbonate (7.25 g) in one go. The reaction was heated to 60° C. for 1.5 hours. A solution of tetrahydro-3-furanylmethyl methanesulfonate, Isomer 2 (2.6 g) in dry N,N-dimethylformamide (3 ml) was added via a Pasteur pipette and the reaction heated at 70° C. for 16 hours. The reaction was cooled to room temperature, diluted with ethyl acetate (100 ml) and washed with brine (20 ml). The organic layer was concentrated in vacuo. The product was purified by C18 reverse phase chromatography using water (0.1% formic acid)-acetonitrile (0.05% formic acid) as eluant (10-60%) to afford the title compound as a clear viscous oil (3 g).

Aufarbeitung

  1. temperaturethe reaction heated at 70° C. for 16 hours
  2. temperatureThe reaction was cooled to room temperature
  3. washwashed with brine (20 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-1a637a32dbec4729852269de4ac157ba
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977344B2

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