Potassium Carbonate → HCID 178508694, Verbindung

HRID 736636Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 736636
[SH:1][C:2]1[NH:10][C:9]2[C:4](=[N:5][CH:6]=[N:7][C:8]=2[NH2:11])[N:3]=1.Br[C:13]1[C:21]([Br:22])=[CH:20][C:16]2[O:17][CH2:18][O:19][C:15]=2[CH:14]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Br:22][C:21]1[C:13]([S:1][C:2]2[NH:3][C:4]3[C:9]([N:10]=2)=[C:8]([NH2:11])[N:7]=[CH:6][N:5]=3)=[CH:14][C:15]2[O:19][CH2:18][O:17][C:16]=2[CH:20]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 2258145,6-Dibromo-1,3-dioxaindaneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 178508691HCID 178508691, Verbindung

Produkt 1

HCID 178508694HCID 178508694, VerbindungAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 250 mL flask was charged with 8-mercaptoadenine (2.00 g, 11.98 mmol), 5,6-dibromo-benzo-[1,3]dioxole (6.70 g, 24.0 mmol), Pd2dba3 (0.548 g, 0.599 mmol), Xantphos (0.693 g, 1.20 mmol), K2CO3 (3.31 g, 23.95 mmol), and dry dioxane (25 mL). The resulting mixture was heated at 100° C. for 16 h under nitrogen. After cooling, the reaction mixture was filtered and washed with a 2/2/0.5 mixture of CH2Cl2, EtOAc, and MeOH. The combined filtrates were concentrated in vacuo. The dark brown residue was purified by chromatography on SiO2 (CH2Cl2/EtOAc/MeOH, 2/2/0/5) and subsequent recrystallization from MeOH provided the title compound (1.4 g, 32%). 1H NMR (DMSO-d6) δ 8.08 (s, 1H), 7.38 (s, 1H), 7.23 (s, 1H), 6.12 (s, 2H).

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. washwashed with a 2/2/0.5 mixture of CH2Cl2, EtOAc, and MeOH
  4. concentrationThe combined filtrates were concentrated in vacuo
  5. customThe dark brown residue was purified by chromatography on SiO2 (CH2Cl2/EtOAc/MeOH, 2/2/0/5) and subsequent recrystallization from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-cd8349957e294ff19778321a08b1df9f
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595401B2

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