Triethylamine → 5-Bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine

HRID 272044Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272044
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.C(N(CC)CC)C.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19]>CN(C=O)C.[Pd].[Cu]I>[Br:8][C:6]1[N:7]=[C:2]([C:22]#[C:21][Si:18]([CH3:20])([CH3:19])[CH3:17])[C:3]([NH2:9])=[N:4][CH:5]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 6200042-Amino-3,5-dibromopyrazine

Produkt 1

HCID 533931895-Bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amineAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 3,5-Dibromo-pyrazin-2-ylamine (3.00 g, 11.86 mmol) in DMF (35 ml) was added triethylamine (16 ml), then tetrakistriphenylphine palladium (0) (685 mg, 0.59 mmol) and copper(I) iodide (271 mg, 1.42 mmol) were added sequentially. Finally trimethylsilylacetylene (2.0 ml, 14.3 mmol) was added dropwise. The reaction mixture was stirred at 120° C. for 30 minutes and then directly adsorbed onto silica gel. Purification by flash chromatography on silica gel with a gradient of ethyl acetate/hexane afforded the title compound (2.30 g, 71% yield) as yellow oil. MS: m/z 270.0/272.0 [MH+].

Aufarbeitung

  1. customPurification by flash chromatography on silica gel with a gradient of ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-2684c15dcc2e477c981aa9c963d43c2a
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452993B2

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