Dimethylformamide → (R)-4-tert-butyl-1-((tetrahydrofuran-2-yl)methyl)pyridin-2(1H)-imine
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CN(C)[CH:14]=[O:15]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([C:5]1[CH:10]=[CH:9][N:8]([CH2:2][C@H:1]2[CH2:5][CH2:6][CH2:14][O:15]2)[C:7](=[NH:11])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
A mixture of 4-tert-butylpyridin-2-amine (1.0 g, 6.7 mmol, LeadGen Labs), Example 11A (2.0 g, 8.0 mmol), and tetrabutylammonium iodide (1.2 g, 3.3 mmol) in N,N-dimethylformamide (1.3 mL) was heated at 95° C. for 16 h. The reaction was incomplete as monitored by LC/MS. One more equivalent of both Example 11A and tetrabutylammonium iodide were added. After stirring at 95° C. for 16 h, the reaction mixture was cooled and quenched with saturated NaHCO3 (10 mL). The aqueous layer was extracted with dichloromethane (3×30 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to provide the title compound. MS (ESI+) m/z 235 (M+H)+.
Workup
- temperaturethe reaction mixture was cooled
- customquenched with saturated NaHCO3 (10 mL)
- extractionThe aqueous layer was extracted with dichloromethane (3×30 mL)
- dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-c0068edc8fed4c38b317df6b879b6027
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193713B2
Reaction notes
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