Dimethylformamide → HCID 68650730, compound

HRID 646742Notes

Reaction equation

HRID 646742 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([NH:11][CH3:12])=[O:10])=[N:4][C:5](Br)=[CH:6][N:7]=1.[Cu][C:14]#[N:15].CN(C=O)C>C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([C:9]([NH:11][CH3:12])=[O:10])=[N:4][C:5]([C:14]#[N:15])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 151481213-Amino-6-bromo-N-methylpyrazine-2-carboxamideHCID 178418546HCID 178418546, compound

Product 1

HCID 68650730HCID 68650730, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Amino-6-bromo-N-methylpyrazine-2-carboxamide (2.0 g, 8.7 mmol) and copper (I) cyanide (3.9 g, 43.5 mmol) were taken into DMF (20 mL) and the mixture was heated to reflux for two hours. The mixture was allowed to cool to room temperature then diluted with ethyl acetate (250 mL). The insoluble residue was removed by filtration and the filtrate partitioned with water. The organic layer was separated and washed with water (2×) then brine and dried over anhydrous magnesium sulfate. Filtration and concentration afforded 3-amino-6-cyano-N-methylpyrazine-2-carboxamide (500 mg, 33% yield) as a white solid: 1H NMR (400 MHz, d6-DMSO): 8.84 (br m, 1H), 8.67 (br s, 1H), 8.65 (s, 1H), 2.77 (d, 3H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for two hours
  3. customThe insoluble residue was removed by filtration
  4. customthe filtrate partitioned with water
  5. customThe organic layer was separated
  6. washwashed with water (2×)
  7. dry with materialbrine and dried over anhydrous magnesium sulfate
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-fc817011d1ec4569bfaeab24b7aa6f71
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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