Water → Methanone, [2-(butylamino)-3-pyridinyl](3-methoxyphenyl)-
Reaction equation
[H-].[Na+].NC1C(C2(OC)C=CC=[C:12]([C:16]([C:18]3C[C:20]([O:31]C)([C:24]4[C:25]([NH2:30])=[N:26][CH:27]=[CH:28][CH:29]=4)[CH:21]=[CH:22][CH:23]=3)=[O:17])C2)=CC=CN=1.[CH2:35](I)[CH2:36][CH2:37][CH3:38].O.O1CCC[CH2:42]1>>[CH2:35]([NH:30][C:25]1[C:24]([C:20](=[O:31])[C:21]2[CH:22]=[CH:23][CH:18]=[C:16]([O:17][CH3:42])[CH:12]=2)=[CH:29][CH:28]=[CH:27][N:26]=1)[CH2:36][CH2:37][CH3:38]Participants
Conditions
- Temperature
- 55 °C
Procedure
To a suspension of sodium hydride (60%, 578 mg, 14.5 mmol) in tetrahydrofuran (15 ml) was added dropwise a solution of 3-(2-aminopyridyl)-(3-methoxyphenyl)ketone (3.00 g, 13.1 mmol) in tetrahydrofuran (24 ml) under ice-cooling, and further thereto was added dropwise a solution of butyl iodide (3.63 g, 19.7 mmol) in tetrahydrofuran at room temperature, and the mixture was stirred at 50-60° C. for 6 hours. The mixture was cooled to room temperature, and thereto was added water. The mixture was extracted with toluene, and washed successively with a 5% aqueous sodium hydrogen carbonate solution, water and a 5% aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=¼) to give the title compound (2.96 g, 10.4 mmol, 79%) as yellow oil.
Workup
- temperaturecooling
- temperatureThe mixture was cooled to room temperature
- extractionThe mixture was extracted with toluene
- washwashed successively with a 5% aqueous sodium hydrogen carbonate solution, water
- dry with materiala 5% aqueous sodium chloride solution, dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=¼)
Sources & evidence
- ORD record
- ord-90dd0e8733444f41a9d93ab9a86a108c
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06452008B2
Reaction notes
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