Hydrazine → 3-Amino-6-chloro-5-hydrazino-pyrazine-2-carboxylic acid methyl ester
Reaction equation
[NH2:1][C:2]1[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:4][C:5]([Cl:9])=[C:6](Cl)[N:7]=1.[NH2:14][NH2:15].CO.C(Cl)Cl>C(O)(C)(C)C.CN(C=O)C>[CH3:13][O:12][C:10]([C:3]1[C:2]([NH2:1])=[N:7][C:6]([NH:14][NH2:15])=[C:5]([Cl:9])[N:4]=1)=[O:11]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
Methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (1.10 g, 5 mmol) was dissolved in 20 mL of tert-butyl alcohol and DMF (v/v; 1:1). Anhydrous hydrazine (0.18 mL, 5.5 mmol) and N,N'-diisopropylethyl amine (4.5 mL, 25 mmol) were then added sequentially at 25° C. The resulting mixture was stirred at 25° C. for 12 h. The reaction mixture was then partitioned between EtOAc (100 mL) and sat. NaCl (aq) (100 mL). The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo to give a brown solid residue. This residue was used in the next-step reaction without further purification: TLC (Rf =0.53; 10% MeOH/CH2Cl2).
Workup
- customThe reaction mixture was then partitioned between EtOAc (100 mL) and sat. NaCl (aq) (100 mL)
- dry with materialThe organic layer was dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give a brown solid residue
- customThis residue was used in the next-step reaction without further purification
Sources & evidence
- ORD record
- ord-3df39bd3e3f941c2a6a496870cdbcb92
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06156758
Reaction notes
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