Dimethylformamide → 6-chloropyrazine-2-carboxamide
Reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[C-]#N.[K+].C[N:13]([CH:15]=[O:16])C>O>[Cl:8][C:4]1[N:3]=[C:2]([C:15]([NH2:13])=[O:16])[CH:7]=[N:6][CH:5]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 2,6-dichloropyrazine (50 mg, 0.34 mmol) in DMF (1 mL) was added a solution of potassium cyanide (24 mg, 0.37 mmol) in H2O (1 mL). After stirring for 3 h at 100° C., the reaction mixture was cooled to r.t., poured into H2O (10 mL) and extracted with EtOAc three times. The combined organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel, EtOAc:Hexane, 3:7) to give 15 mg of the desired product. Yield: 32%.
Workup
- temperaturethe reaction mixture was cooled to r.t.
- extractionextracted with EtOAc three times
- dry with materialThe combined organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by column chromatography (silica gel, EtOAc:Hexane, 3:7)
Sources & evidence
- ORD record
- ord-9e0f0398cae6462da726ec20f7bfbc89
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07601742B2
Reaction notes
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