Acetic Acid → 6-chloro-N-(cyclopropylmethyl)-2-methylpyridin-3-amine

In a dry flask, 6-chloro-2-methylpyridin-3-amine (200 mg, 1.40 mmol) and cyclopropanecarbaldehyde (116 μl, 1.54 mmol) were taken up in 1,2-dichloroethane (5.6 ml) under argon. The resulting clear solution was stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.47 g, 2.10 mmol) and acetic acid (160 μl, 2.81 mmol) were sequentially added to the reaction mixture, which was stirred as such for 24 hours. The reaction mixture was quenched with aqueous sodium bicarbonate and extracted three times with dichloromethane. All organic fractions were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated. The resulting crude product was purified by silica gel chromatography (0-50% ethyl acetate/hexanes) to afford the title compound.

1. stirringwas stirred as such for 24 hours
2. customThe reaction mixture was quenched with aqueous sodium bicarbonate
3. extractionextracted three times with dichloromethane
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe resulting crude product was purified by silica gel chromatography (0-50% ethyl acetate/hexanes)

ORD record

ord-ceb99825996748f0b6c9ced877d92b28

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2