Chloroform → 5-Aminopyrazine-2-carbonitrile

HRID 1830768Notes

Reaction equation

HRID 1830768 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.C1OCCOCCOCCOCCOCCOC1.[C-:27]#[N:28].[K+].C(Cl)(Cl)Cl>CN(C)C=O.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:8][C:5]1[CH:4]=[N:3][C:2]([C:27]#[N:28])=[CH:7][N:6]=1

Participants

8

Reactant 4

HCID 6212ChloroformHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 5995392-Amino-5-bromopyrazine

Product 1

HCID 139252945-Aminopyrazine-2-carbonitrileYield 60%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-bromo-2-aminopyrazine (1.0 g) 5.8 mmol), CuI (2.76 g, 14.5 mmol), 18-crown-6 (121 mg; 0.46 mmol), potassium cyanide (943 mg; 14.5 mmol) in dimethylformamide (20 mL) was added Pd(PPh3)4 (196 mg; 0.17 mmol). After stirring at room temperature for 20 minutes the reaction was placed in an oil bath at 155° C. for 2 hours. The reaction was allowed to cool to room temperature and then poured into chloroform (300 mL). A precipitate formed that was filtered and triturated with hexanes to yield an off white solid (60% yield).

Workup

  1. waitwas placed in an oil bath at 155° C. for 2 hours
  2. temperatureto cool to room temperature
  3. customA precipitate formed
  4. filtrationthat was filtered
  5. customtriturated with hexanes

Sources & evidence

ORD record
ord-e4d7db70948d4c77913030a7bcda028f
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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