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

HRID 272044ノート

反応式

HRID 272044 の反応式
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

参加物

7

反応物 3

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

生成物 1

HCID 533931895-Bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine収率 71.8%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

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+].

後処理

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

出典と根拠

ORDレコード
ord-2684c15dcc2e477c981aa9c963d43c2a
出典データセット
uspto-grants-2008_11
特許番号
US07452993B2

反応ノート

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