N-bromobutanimide → 2-(5-Amino-6-bromopyrazin-2-yl)ethanol
Reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][CH2:9][OH:10])=[N:6][CH:7]=1.C1C(=O)N([Br:18])C(=O)C1>CC#N>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][CH2:9][OH:10])=[N:6][C:7]=1[Br:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-(5-aminopyrazin-2-yl)ethanol (30 mg, 0.216 mmol) in CH3CN (719 μL) was added NBS (38.4 mg, 0.216 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 30 min. The reaction mixture was quenched by sat. NaHCO3, then extracted by EtOAc, The combined organic layer was washed with water and brine, dried over anhydrous sodium sulfate. Filtered and concentrated in vacuo yielding crude 2-(5-amino-6-bromopyrazin-2-yl)ethanol which was used in next step reaction without purification. LCMS (m/z): 218.0/220.0 (MH+), 0.33 min.
Workup
- customThe reaction mixture was quenched by sat. NaHCO3
- extractionextracted by EtOAc
- washThe combined organic layer was washed with water and brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationFiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8a4574e641db47e891c13ebf93686b17
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242996B2
Reaction notes
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