Sodium Carbonate → 2-(3-(3-(4-Chlorophenyl)pyrazin-2-YL)azetidin-1-YL)quinazoline

HRID 1850328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1850328
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]1[C:9]([CH:14]2[CH2:17][N:16]([C:18]3[N:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)[CH2:15]2)=[N:10][CH:11]=[CH:12][N:13]=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:8]2[C:9]([CH:14]3[CH2:17][N:16]([C:18]4[N:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:31][CH:30]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 585467542-(3-(3-Chloropyrazin-2-yl)azetidin-1-yl)quinazoline

Produkt 1

HCID 585468062-(3-(3-(4-Chlorophenyl)pyrazin-2-YL)azetidin-1-YL)quinazolineAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2M aqueous sodium carbonate (0.378 mL, 0.756 mmol, J. T. Baker) was added to a stirred mixture of 2-(3-(3-chloropyrazin-2-yl)azetidin-1-yl)quinazoline (0.075 g, 0.252 mmol, Preparation 1), trans-dichlorobis(triphenylphosphine)palladium (ii) (0.009 g, 0.013 mmol, Strem), and 4-chlorophenylboronic acid (0.047 g, 0.302 mmol, ASDI) in 1,4-dioxane (1 mL) in a sealed tube under an argon atmosphere. The reaction mixture was stirred at 80° C. for 17 h. The reaction mixture was concentrated in vacuo and diluted with DCM. The resulting suspension was filtered, and the filtrate was concentrated in vacuo. The resulting crude material was purified via reverse phase HPLC (Column: Xbridge 19×100 mm, 5 μm, 1771302301) eluting with 0.1% NH4OH in acetonitrile/water to give 0.060 g (64%) of a yellow amorphous solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with DCM
  3. filtrationThe resulting suspension was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe resulting crude material was purified via reverse phase HPLC (Column: Xbridge 19×100 mm, 5 μm, 1771302301)
  6. washeluting with 0.1% NH4OH in acetonitrile/water

Quellen und Nachweise

ORD-Eintrag
ord-0b2872c9e14c4b98b7a74825f2018e79
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957073B2

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