Potassium tert-butoxide → HCID 44608447, compound
Reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[C:5]([C:10]#[C:11][CH:12]([CH3:14])[CH3:13])[CH:4]=1.CC([O-])(C)C.[K+]>CN1CCCC1=O>[CH:12]([C:11]1[NH:9][C:6]2=[CH:7][N:8]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[CH:10]=1)([CH3:14])[CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
To a solution of 6-methoxy-4-(3-methylbut-1-ynyl)pyridin-3-amine (Compound 4, 588 mg, 3.1 mmol) in N-methylpyrrolidone (10 ml) was added KOtBu (0.87 g, 7.8 mmol) at room temperature. The mixture was heated to 140° C. for 0.5 h and cooled to room temperature, quenched with H2O, extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound as light brown syrup.
Workup
- temperaturecooled to room temperature
- customquenched with H2O
- extractionextracted with EtOAc
- washThe organic layer was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)
Sources & evidence
- ORD record
- ord-52c6a17ca1474864b128fb0d2f417aff
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012992B2
Reaction notes
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