N-bromobutanimide → 5-Bromo-6-chloropyrazin-2-amine
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[N:4][CH:3]=1.[Br:9]N1C(=O)CCC1=O>C(Cl)Cl>[Br:9][C:3]1[N:4]=[CH:5][C:6]([NH2:8])=[N:7][C:2]=1[Cl:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
6-Chloropyrazin-2-amine (2.50 g, 19.3 mmol) was stirred in CH2Cl2 (60 mL) at 0° C. N-Bromosuccinimide (2.92 g, 16.4 mmol) was added slowly and the reaction mixture was stirred at 0° C. for 60 minutes. The reaction mixture was filtered through celite and concentrated to give a brown oil. Purification by flash chromatography, eluting with 0-25% EtOAc-hexanes, gave 5-bromo-6-chloropyrazin-2-amine as a yellow solid (1.69 g, 8.16 mmol, 42% yield).
Workup
- filtrationThe reaction mixture was filtered through celite and
- concentrationconcentrated
- customto give a brown oil
- customPurification by flash chromatography
- washeluting with 0-25% EtOAc-hexanes
Sources & evidence
- ORD record
- ord-52fc5468d2b74a50bfdd11b5eed2d9c6
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040540B2
Reaction notes
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