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

HRID 1713002

反応式

HRID 1713002 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-f28f29cf42754ab08b61aa342508e942
出典データセット
uspto-grants-2010_09
特許番号
US07795259B2

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