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

HRID 384642Notes

Reaction equation

HRID 384642 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

HCID 59613433HCID 59613433, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a9694d9ce95a4080ba633b35d4919f5c
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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