Potassium Carbonate → cis-4-(6-Chloro-2-pyrazinyl)-2,6-dimethylmorpholine
Reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.[Cl:9][C:10]1[CH:15]=[N:14][CH:13]=[C:12](Cl)[N:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:9][C:10]1[N:11]=[C:12]([N:4]2[CH2:5][C@H:6]([CH3:8])[O:7][C@H:2]([CH3:1])[CH2:3]2)[CH:13]=[N:14][CH:15]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
cis-2,6-Dimethylmorpholine (0.850 g, 7.38 mmol) was added to a suspension of 2,6-dichloropyrazine (1 g, 6.71 mmol) and potassium carbonate (2.78 g, 20.14 mmol) in anhydrous acetonitrile (50 mL). After addition, the reaction mixture was stirred at 90° C. for 3 hours. Crude LCMS showed desired product can be seen and no starting material left, so the reaction mixture was diluted with ethyl acetate (100 mL) and water (50 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layer was dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was dissolved in dichloromethane (˜10 ml) and purified on silica by a Biotage SP4 chromatographic system (40+M cartridge, eluted with 0-100% ethyl acetate in isohexanes). Fractions containing the pure product were combined and concentrated under reduced pressure to give the title compound as a white solid (742 mg, 3.10 mmol, 46.1% yield). LC/MS [M+H]+=228/230.
Workup
- additionAfter addition
Sources & evidence
- ORD record
- ord-4d335652ed0f452985e8e5c79782bb2c
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133178B2
Reaction notes
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