Trimethyl-2-propynylsilane → 5-Bromo-3-(3-trimethylsilanyl-prop-1-ynyl)-pyrazin-2-ylamine

HRID 905985

反応式

HRID 905985 の反応式
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[CH3:10][Si:11]([CH3:16])([CH3:15])[CH2:12][C:13]#[CH:14]>C1COCC1.CCOC(C)=O.[Cu]I>[Br:8][C:6]1[N:7]=[C:2]([C:14]#[C:13][CH2:12][Si:11]([CH3:16])([CH3:15])[CH3:10])[C:3]([NH2:9])=[N:4][CH:5]=1

参加物

6

反応物 2

HCID 83378Trimethyl-2-propynylsilaneHCID 6200042-Amino-3,5-dibromopyrazine

生成物 1

HCID 866423045-Bromo-3-(3-trimethylsilanyl-prop-1-ynyl)-pyrazin-2-ylamine収率 87.2%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3,5-Dibromo-pyrazin-2-ylamine (1.70 g, 6.70 mmol), TEA (1.1 mL, 8.04 mmol), PdCl2(PPh3)4 (28 mg, 0.040 mmol), and CuI (15 mg, 0.080 mmol) were dissolved in THF (17 mL), cooled to RT and Trimethyl-prop-2-ynyl-silane (1.0 mL, 6.7 mmol) was added at 0° C., allowed to warm up to RT and stirred overnight. The reaction mixture was diluted with EtOAc, washed with H2O and saturated aqueous NaHCO3, dried (MgSO4) and concentrated, and purified by SiO2 chromatography (80 g SiO2, hexanes/EtOAc 0-35% EtOAc) to give 1.66 g of 5-bromo-3-(3-trimethylsilanyl-prop-1-ynyl)-pyrazin-2-ylamine as a yellow semi-solid contaminated by starting material (87% yield, 66% purity).

後処理

  1. temperatureto warm up to RT
  2. washwashed with H2O and saturated aqueous NaHCO3
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by SiO2 chromatography (80 g SiO2, hexanes/EtOAc 0-35% EtOAc)

出典と根拠

ORDレコード
ord-e6cbde8d04c7467f824533ee652c141d
出典データセット
uspto-grants-2011_09
特許番号
US08012974B2

関連ノート

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