Dimethylformamide → 3-Azido-2,5-dimethylpyrazine
Reaction equation
Cl[C:2]1[C:7](C)=[N:6][C:5]([CH3:9])=[CH:4][N:3]=1.[N-:10]=[N+:11]=[N-:12].[Na+].[CH3:14]N(C)C=O>C(OCC)(=O)C>[N:10]([C:7]1[C:2]([CH3:14])=[N:3][CH:4]=[C:5]([CH3:9])[N:6]=1)=[N+:11]=[N-:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a stirred solution of 2-chloro-3,5-dimethyl pyrazine (1.0 mL; 8.3 mmol) in dimethylformamide (10 ml,) was added sodium azide (539 mg; 8.3 mmol). The reaction was heated to 100° C. and stirred for 12 hours. The reaction was cooled to room temperature, diluted with 50 mL of ethyl acetate and washed with aqueous 10% sodium carbonate (1×50 mL), brine (50 mL), then dried (MgSO4), and filtered. The material was purified using a biotage 12L cartridge eluting with hexanes and ethyl acetate (3: 1) to yield an off white solid (42% yield).
Workup
- temperatureThe reaction was cooled to room temperature
- washwashed with aqueous 10% sodium carbonate (1×50 mL), brine (50 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customThe material was purified
- washeluting with hexanes and ethyl acetate (3: 1)
Sources & evidence
- ORD record
- ord-d72245b6c8d246be83e74d1cf5b0b063
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07067506B2
Reaction notes
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