N-bromobutanimide → 5-bromo-3,6-diethyl-N-(1-ethylpropyl)pyrazin-2-amine
Reaction equation
[CH2:1]([C:3]1[C:4]([NH:11][CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[N:5][C:6]([CH2:9][CH3:10])=[CH:7][N:8]=1)[CH3:2].[Br:17]N1C(=O)CCC1=O>C(Cl)Cl>[Br:17][C:7]1[N:8]=[C:3]([CH2:1][CH3:2])[C:4]([NH:11][CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[N:5][C:6]=1[CH2:9][CH3:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A 500 mL dry round bottom flask equipped with a magnetic stir bar was charged with 3,6-diethyl-N-(1-ethylpropyl)pyrazin-2-amine (10.0 g, 45.18 mmol) and CH2Cl2 (220 mL). After the mixture was cooled with an ice bath, N-bromosuccinimide (8.84 g, 49.7 mmol) was added at once. The mixture was stirred at 0° C. for 30 minutes then quenched with saturated aq. NaHCO3, diluted with H2O and extrated twice with CH2Cl2. The organics were combined, dried with NaSO4, filtered and concentrated to 13.96 g of a brown oil. The crude was purified by Biotage MPLC in two batches (120 g columns, 2.5% ethyl acetate in heptane.) Like fractions were combined to give 11.57 g (85%) of 5-bromo-3,6-diethyl-N-(1-ethylpropyl)pyrazin-2-amine as a yellow oil.
Workup
- customA 500 mL dry round bottom flask
- customequipped with a magnetic stir bar
- temperatureAfter the mixture was cooled with an ice bath
- customthen quenched with saturated aq. NaHCO3
- additiondiluted with H2O
- dry with materialdried with NaSO4
- filtrationfiltered
- concentrationconcentrated to 13.96 g of a brown oil
- customThe crude was purified by Biotage MPLC in two batches (120 g columns, 2.5% ethyl acetate in heptane.) Like fractions
Sources & evidence
- ORD record
- ord-8a0a127bce17497db1e3420c840ac7d7
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06964965B2
Reaction notes
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