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

HRID 386406

반응식

HRID 386406 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-2047b6b997224694964515edb1f25e62
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372835B2

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