Potassium Carbonate → (S)-N-(1-(3-aminophenyl)ethyl)-6-chloropyrazin-2-amine

HRID 1255825

Reaktionsgleichung

Reaktionsgleichung von HRID 1255825
[NH2:1][C@H:2]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])[CH3:3].[Cl:11][C:12]1[CH:17]=[N:16][CH:15]=[C:14](Cl)[N:13]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[NH2:7][C:6]1[CH:5]=[C:4]([C@@H:2]([NH:1][C:14]2[CH:15]=[N:16][CH:17]=[C:12]([Cl:11])[N:13]=2)[CH3:3])[CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 785042,6-DichloropyrazineHCID 40637894(S)-3-(1-aminoethyl)aniline

Produkt 1

HCID 25218447(S)-N-(1-(3-aminophenyl)ethyl)-6-chloropyrazin-2-amineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 3-[(1S)-1-aminoethyl]aniline (7.5 g, 55 mmol), 2,6-dichloropyrazine (12.3 g, 82.5 mmol) and potassium carbonate (15.2 g, 110 mmol) in dioxane (140 mL) was heated at reflux for 3 days. After this time the mixture was cooled to room temperature, filtered and concentrated under reduced pressure to give an orange oil which was purified by flash chromatography (silica, ethyl acetate/hexanes) to give N-[(1S)-1-(3-aminophenyl)ethyl]-6-chloropyrazin-2-amine (11.6 g, 85%) as a beige solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 3 days
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give an orange oil which
  6. customwas purified by flash chromatography (silica, ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-fd8910db71994befa8cd12c879b88922
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461161B2

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