Potassium Cyanide → 5-Aminopyrazine-2-carbonitrile

HRID 418008Notes

Reaction equation

HRID 418008 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[C-:9]#[N:10].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C.[Cu]I>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:9]#[N:10])=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 5995392-Amino-5-bromopyrazine

Product 1

HCID 139252945-Aminopyrazine-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
155 °C

Procedure

5-Bromo-pyrazin-2-ylamine was combined with copper (I) iodide (1.3 g, 6.9 mmol), potassium cyanide (0.44 g, 6.8 mmol), tetrakis (triphenylphosphine)palladium(0) (0.95 g, 0.83 mmol), and 18-crown-6 (0.058 g, 0.22 mmol) in DMF (15 mL). The resulting mixture was stirred for 40 min, then heated at reflux (155° C.) for 2 h. The reaction was cooled to room temperature, then allowed to stand overnight. The precipitate was separated by filtration and the filtrate was concentrated to dryness in vacuo. The orange-colored residue was taken up in EtOAc and hexanes and an initial precipitate was formed, then separated by filtration. Upon standing, additional precipitate formed in the mother liquor and was collected by filtration. The solids were combined to yield 0.10 g of a bright orange solid.

Workup

  1. temperatureheated
  2. temperatureThe reaction was cooled to room temperature
  3. waitto stand overnight
  4. customThe precipitate was separated by filtration
  5. concentrationthe filtrate was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-f475970fbfcc4fed969f1b12afec5db8
Source dataset
uspto-grants-2012_01
Patent number
US08093244B2

Reaction notes

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