2-Amino-5-bromopyrazine → HCID 59613433, 화합물

HRID 556801노트

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HRID 556801 반응식
[NH2:1][C:2]1[CH:7]=[N:6][C:5](Br)=[CH:4][N:3]=1.[C:9]([Si:13]([CH3:19])([CH3:18])[O:14][CH2:15][C:16]#[CH:17])([CH3:12])([CH3:11])[CH3:10]>[Cu]I.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[N:6][C:5]([C:17]#[C:16][CH2:15][O:14][Si:13]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:18])[CH3:19])=[CH:4][N:3]=1

참가 물질

5

반응물 2

HCID 5995392-Amino-5-bromopyrazineHCID 3445622tert-Butyl(dimethyl)[(prop-2-yn-1-yl)oxy]silane

생성물 1

HCID 59613433HCID 59613433, 화합물수율 91%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매

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온도
60 °C

실험 절차

2-Amino-5-bromopyrazine (1.50 g, 8.6 mmol) was dissolved in anhydrous, deoxygenated DMF (24.5 mL) with triethylamine (10.5 mL). Copper(I) iodide (0.33 g, 1.7 mmol), tetrakis(triphenylphosphine)-palladium(0) (0.61 g, 0.51 mmol) and tert-butyldimethyl(prop-2-ynyloxy)silane (1.90 g, 11.2 mmol) were added and the solution was stirred overnight at 60° C., then cooled and partitioned between water and dichloromethane. The aqueous phase was extracted with dichloromethane and the combined organic phases were dried (Na2SO4) and evaporated. The residue was purified by silica chromatography to give 2-amino-5-(3-(tert-butyldimethylsilyloxy)prop-1-ynyl)pyrazine (2.06 g, 91%) as a brown solid.

후처리

  1. customdeoxygenated DMF (24.5 mL) with triethylamine (10.5 mL)
  2. temperaturecooled
  3. custompartitioned between water and dichloromethane
  4. extractionThe aqueous phase was extracted with dichloromethane
  5. dry with materialthe combined organic phases were dried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified by silica chromatography

출처 및 근거

ORD 기록
ord-e63d3d00994846518e0c3096e58032eb
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058045B2

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