Dimethylformamide → HCID 10080539, compound

To a solution of 5-amino-3-cyanopyridine (0.50 g, 4.20 mmol) in DMF (5 ml) was added NaH (60% in oil) (0.37 g, 9.26 mmol) under ice-cooling, and the mixture was stirred for 20 minutes. Methyl iodide (0.58 ml, 9.31 mmol) in DMF (2 ml) was added dropwise under ice-cooling. The mixture was stirred for 2 hours while the temperature was raised up to room temperature. Ice was added to the reaction mixture, and the mixture was extracted with diethyl ether (30 ml×3). The diethyl ether layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (Wako Gel C-200, 20 g; eluted with chloroform:methanol=200:1) to give 3-cyano-5-dimethylaminopyridine (145 mg, yield 23%).

1. temperaturecooling
2. temperaturecooling
3. stirringThe mixture was stirred for 2 hours while the temperature
4. additionIce was added to the reaction mixture
5. extractionthe mixture was extracted with diethyl ether (30 ml×3)
6. washThe diethyl ether layer was washed with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue thus obtained
10. customwas purified by silica gel column chromatography (Wako Gel C-200, 20 g; eluted with chloroform:methanol=200:1)

ORD record

ord-fbb09ccc32004766802c9614a8e3a7bb

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05508293