Ethyl orthoformate → ethyl [5-(1H-tetrazol-1-yl)pyrazin-2-yl]acetate
Reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:6][CH:7]=1.[CH:14](OCC)(OCC)OCC.[N-:24]=[N+:25]=[N-:26].[Na+]>CC(O)=O>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][C:5]1[CH:4]=[N:3][C:2]([N:1]2[CH:14]=[N:26][N:25]=[N:24]2)=[CH:7][N:6]=1)[CH3:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A solution of the ethyl (5-aminopyrazin-2-yl)acetate (2.0 g, 11.0 mmol) and triethyl orthoformate (4.9 g, 33.1 mmol) in 60 mL of HOAc was added sodium azide (0.9 g, 13.8 mmol) and heated to 100° C. for 1 hour. The reaction was completed which was checked by TLC. The reaction mixture was cooled to r.t. The solvent was removed under vacuum. The residue was dissolved in EtOAc, washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatograph to afford the product ethyl[5-(1H-tetrazol-1-yl)pyrazin-2-yl]acetate.
Workup
- temperatureThe reaction mixture was cooled to r.t
- customThe solvent was removed under vacuum
- dissolutionThe residue was dissolved in EtOAc
- washwashed with water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe residue was purified by column chromatograph
Sources & evidence
- ORD record
- ord-5b9c713885274acfada952f441206192
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206199B2
Reaction notes
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