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

HRID 905985

반응식

HRID 905985 반응식
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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e6cbde8d04c7467f824533ee652c141d
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012974B2

연결된 노트

불러오는 중…