Sodium Cyanide → 3-Amino-6-bromopyrazine-2-carbonitrile

HRID 1184823Notes

Reaction equation

HRID 1184823 reaction equation
[Cu][C:2]#[N:3].[C-]#N.[Na+].[NH2:7][C:8]1[C:13](Br)=[N:12][C:11]([Br:15])=[CH:10][N:9]=1>CN(C=O)C>[NH2:7][C:8]1[C:13]([C:2]#[N:3])=[N:12][C:11]([Br:15])=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 6200042-Amino-3,5-dibromopyrazineHCID 178418546HCID 178418546, compound

Product 1

HCID 110526113-Amino-6-bromopyrazine-2-carbonitrileYield 67.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A solution of copper(i) cyanide (1.20 g, 13.42 mmol) and sodium cyanide (0.658 g, 13.42 mmol) in DMF (10 mL) was heated to 125° C. 2-amino-3,5-dibromo pyrazine (2.61 g, 10.32 mmol) was added in portions. The reaction was stirred at 125° C., and after 5 h quenched in ice cold NaHCO3 solution. The black precipitate was filtrated off and the filtrate was extracted (3×) with EtOAc. The organic layer was washed with brine, dried and evaporated. Purification by chromatography (CH2Cl2) gave pure 3-amino-6-bromopyrazine-2-carbonitrile 14 (1.38 g, 67.2%). 1H-NMR (400 MHz, CDCl3) 5.29 (br s, 2H), 8.30 (s, 1H). (m/z)=199 and 201 (M+H)+.

Workup

  1. customafter 5 h quenched in ice cold NaHCO3 solution
  2. filtrationThe black precipitate was filtrated off
  3. extractionthe filtrate was extracted (3×) with EtOAc
  4. washThe organic layer was washed with brine
  5. customdried
  6. customevaporated
  7. customPurification by chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-5bc2cac445d24db4a6e46199fe3a09ad
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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