HCID 178418268, Verbindung → 6,8-Dibromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazine

HRID 2242887

Reaktionsgleichung

Reaktionsgleichung von HRID 2242887
[Br:1][C:2]1[C:3]([NH:9][C:10]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)=[NH:11])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C1(C)C=CC=CC=1>[Br:8][C:6]1[N:7]=[C:2]([Br:1])[C:3]2[N:4]([N:11]=[C:10]([C:12]3[O:13][CH:14]=[CH:15][CH:16]=3)[N:9]=2)[CH:5]=1

Komponenten

4

Edukt 2

HCID 178418268HCID 178418268, VerbindungHCID 178512066HCID 178512066, Verbindung

Produkt 1

HCID 860075466,8-Dibromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazineAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of N-(3,5-dibromo-pyrazin-2-yl)-furan-2-carboxamidine (47 g, 0.14 mol), lead tetraacetate (95% purity, 160 g, 0.34 mol), and toluene (940 ml) was refluxed for 2 hours. The reaction was allowed to cool to room temperature and concentrated in vacuo. The resulting residue was purified by flash column chromatography on silica (hexanes:EtOAc (5:1 to 3:1)) as eluent to afford 6,8-dibromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazine as a yellow solid (19.2 g, 40% yield). 1H NMR (300 MHz, CDCl3) δ 6.60 (dd, 1H), 7.33 (d, 1H), 7.62 (d, 1H), 8.63 (s, 1H).

Aufarbeitung

  1. temperaturewas refluxed for 2 hours
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was purified by flash column chromatography on silica (hexanes:EtOAc (5:1 to 3:1)) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-0eaaf5f2ec174970afb48501280d32bc
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07674791B2

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