Pyridine → 3-Benzyl-5-bromopyrazin-2-amine
Reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][CH:5]=[CH:4][N:3]=1.N1C=CC=CC=1.[Br-:21].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:7]([CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[N:6][C:5]([Br:21])=[CH:4][N:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-benzyl-2-aminopyrazine 12 (1.38 g, 7.40 mmol) in chloroform (40 mL), pyridine (1.80 mL, 22.00 mmol) and tetrabutylamoniumtribromide TBATB (3.57 g, 7.40 mmol) were added at room temperature. After 1 h the reaction mixture was washed with 20% aqueous solution of NaCl, the organic layer was then dried over Na2SO4, filtered and the solvent removed under reduced pressure. The crude was purified by flash chromatography (EtOAc-dichloromethane, 80:20) to get 1.75 g (89% yield) of the title compound 13 as a pale brown solid and subsequent recrystallization (n-exane/diethyl ether) gave colorless crystals suitable for crystallographic studies. 1H-NMR (CDCl3): 3.97 (s, 2H), 4.74 (br s, 2H), 7.10-7.24 (m, 5H), 7.89 (s, 1H). MS (ESI): m/z 265 (M+H). The crystallography of compound 13 is shown in FIG. 3, demonstrating its purity.
Workup
- washAfter 1 h the reaction mixture was washed with 20% aqueous solution of NaCl
- dry with materialthe organic layer was then dried over Na2SO4
- filtrationfiltered
- customthe solvent removed under reduced pressure
- customThe crude was purified by flash chromatography (EtOAc-dichloromethane, 80:20)
- customto get
Sources & evidence
- ORD record
- ord-95410e8f9f22433098c094debba439ff
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546147B2
Reaction notes
Loading…