Potassium Carbonate → N2-Butyl-8-methoxy-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-Purine-2,6-diamine

HRID 1010929

Reaktionsgleichung

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+].Br[CH2:32][CH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]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[CH2:32][CH:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a solution of N2-butyl-8-methoxy-9H-purine-2,6-diamine trifluoroacetic acid salt (500 mg) in dry N,N-dimethylformamide (8 ml) at room temperature and under nitrogen was added potassium carbonate (1.17 g) in one go. The reaction was stirred at 60° C. for 1.5 hours and then cooled to room temperature. 4-(bromomethyl)tetrahydro-2H-pyran (0.3 ml) was added in one go and the reaction heated at 50° C. overnight. The reaction was diluted with ethyl acetate (20 ml) and washed with water (10 ml). The organic layer was separated and 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 (10-45%) to afford the title compound as a yellow viscous oil (315 mg, 90% clean).

Aufarbeitung

temperaturecooled to room temperature
temperaturethe reaction heated at 50° C. overnight
washwashed with water (10 ml)
customThe organic layer was separated
concentrationconcentrated in vacuo
customThe product was purified by C18 reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag: ord-2e0643ede0dc4b8686af97d8e6ad8ca4
Quelldatensatz: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07977344B2

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