Benzene, 2-iodo-1,3-dimethyl- → (E)-9-(2,6-dimethylstyryl)-2-chloro-N-(4-(dimethylphosphoryl)phenyl)-9H-purin-6-amine

HRID 2041924

Reaktionsgleichung

[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]=[CH2:12])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([P:20]([CH3:23])([CH3:22])=[O:21])=[CH:16][CH:15]=2)[N:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.I[C:47]1[C:52]([CH3:53])=[CH:51][CH:50]=[CH:49][C:48]=1[CH3:54].CCN(C(C)C)C(C)C>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:54][C:48]1[CH:49]=[CH:50][CH:51]=[C:52]([CH3:53])[C:47]=1/[CH:12]=[CH:11]/[N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([Cl:1])=[N:3][C:4]=2[NH:13][C:14]1[CH:19]=[CH:18][C:17]([P:20]([CH3:22])([CH3:23])=[O:21])=[CH:16][CH:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

To an oven-dried 50 mL round-bottom flask were added 2-chloro-N-(4-(dimethylphosphoryl)phenyl)-9-vinyl-9H-purin-6-amine (0.32 g, 0.93 mmol), Pd(OAc)2 (10 mg, 0.05 mmol), tri-o-tolylphosphine (30 mg, 0.1 mmol), 2-iodo-m-xylene (0.39 g, 1.67 mmol). The mixture was flushed with Ar and then dissolved in ˜10 mL anhydrous DMF. DIEA (0.39 g, 2.79 mmol) was then added via syringe. The reaction was stirred at 110° C. overnight. The reaction was diluted with EtOAc and filtered through celite, washed with ample ˜5% MeOH/EtOAc, the combined organic layer was washed with water twice, dried over Na2SO4. Final product was purified by silica gel column chromatography (4˜8 MeOH/DCM).

Aufarbeitung

customThe mixture was flushed with Ar
dissolutiondissolved in ˜10 mL anhydrous DMF
filtrationfiltered through celite
washwashed with ample ˜5% MeOH/EtOAc
washthe combined organic layer was washed with water twice
dry with materialdried over Na2SO4
customFinal product was purified by silica gel column chromatography (4˜8 MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag: ord-00892d455bcb4e2ba144bdeef61e6749
Quelldatensatz: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08586566B2

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