Triethylamine → 5-Chloro-3-(triethyl-silanylethynyl)-pyrazin-2-ylamine

HRID 1713002

Reaktionsgleichung

Reaktionsgleichung von HRID 1713002
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Cl:8])[N:7]=1.C(N(CC)CC)C.[CH2:17]([Si:19]([C:24]#[CH:25])([CH2:22][CH3:23])[CH2:20][CH3:21])[CH3:18]>[Cu](I)I.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.C1COCC1>[Cl:8][C:6]1[N:7]=[C:2]([C:18]#[C:17][Si:19]([CH2:24][CH3:25])([CH2:22][CH3:23])[CH2:20][CH3:21])[C:3]([NH2:9])=[N:4][CH:5]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 637947(Triethylsilyl)acetyleneHCID 104886093-Bromo-5-chloropyrazin-2-amine

Produkt 1

HCID 594635225-Chloro-3-(triethyl-silanylethynyl)-pyrazin-2-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 250 ml round bottom flask was charged with 3-bromo-5-chloro-pyrazin-2-ylamine (2) (1 g, 4.8 mmol), THF (10 ml), copper iodide (9 mg, 0.05 mM) and PdCl2(PPh3)2 (34 mg, 0.05 mmol) under nitrogen. To the reaction mixture, triethylamine (2 ml, 14.4 mmol) and triethylsilylacetylene (1 ml, 5.76 mmol) were added. The reaction mixture was stirred at room temperature for 3 h, then concentrated in vacuo and the residue was purified by flash chromatography, using as eluent pentane/EtOAc 10% to 30%, to give the title compound as an off white solid (1.2 g, 100%). 1H NMR (CDCl3): 0.7-0.8 (6H, qd), 1.0-1.1 (9H, t), 5.0-5.1 (2H, brs), 7.95 (1H, s). MS (ES+): 268.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f28f29cf42754ab08b61aa342508e942
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795259B2

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