Cyclopropylamine → 3-Bromo-N-cyclopropylimidazo[1,2-a]pyrazin-8-amine
Reaction equation
[Br:1][C:2]1[N:6]2[C:7](Br)=[CH:8][N:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH:12]1([NH2:15])[CH2:14][CH2:13]1.C(N(C(C)C)CC)(C)C>C1COCC1.C(Cl)Cl.O>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH:15][CH:12]3[CH2:14][CH2:13]3)[C:5]2=[N:4][CH:3]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 3,5-dibromo-imidazo[1,2-a]pyrazine (D) (250 mg, 0.9 mmol) in THF (9 ml) was added cyclopropylamine (1.9 ml, 27 mmol) and diisopropylethylamine (DIPEA) (0.782 ml, 4.5 mmol). The mixture was heated at 50° C. in sealed tube overnight. The mixture was then cooled to rt, diluted with DCM and water. The organic layer was washed with brine, dried and concentrated. The residue was purified on a silica gel column to give 33 mg (yield 14.5%) of the title compound.
Workup
- temperatureThe mixture was then cooled to rt
- washThe organic layer was washed with brine
- customdried
- concentrationconcentrated
- customThe residue was purified on a silica gel column
Sources & evidence
- ORD record
- ord-cb98ee9cbba545a4be1c4c10b5f3a263
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07186832B2
Reaction notes
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