2-Amino-3-chloropyrazine → HCID 86670917, Verbindung

HRID 1186491Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186491
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8](Br)[CH:9](OC)OC)[N:3]=1.[Cl:15][C:16]1[C:17]([NH2:22])=[N:18][CH:19]=[CH:20][N:21]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>CC#N.O>[Br:1][C:2]1[N:3]=[C:4]([C:8]2[N:18]3[CH:19]=[CH:20][N:21]=[C:16]([Cl:15])[C:17]3=[N:22][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 2762242-Amino-3-chloropyrazineHCID 521998p-Toluenesulfonic acid monohydrateHCID 866709182-Bromo-6-(1-bromo-2,2-dimethoxy-ethyl)-pyridine

Produkt 1

HCID 86670917HCID 86670917, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 2-bromo-6-(1-bromo-2,2-dimethoxy-ethyl)-pyridine (from Example 37 supra) (5.267 g, 16.2 mmol), 3-chloropyrazin-2-amine (2.1 g, 16.2 mmol), and pTsOH.H2O (2.1 g, 11 mmol) in CH3CN (900 mL) and water (90 mL) was stirred and heated at reflux overnight. The reaction mixture was then cooled to room temperature, concentrated under reduced pressure. The crude product was purified by chromatography (CH2Cl2:CH3OH, 100:1) to give 3-(6-bromo-pyridin-2-yl)-8-chloro-imidazo[1,2-a]pyrazine. (Yield 4.86 g, 52%). LC-MS: [M+H]+ 309.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by chromatography (CH2Cl2:CH3OH, 100:1)

Quellen und Nachweise

ORD-Eintrag
ord-3de223f2cfda423bb3228e612169f1f8
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673905B2

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