Methyl iodide → 2-Chloro-N-methylpyridin-3-amine

Temperature

0 °C

To a solution of 2-chloro-3-pyridinamine (0.0465 mol) in THF (45ml) at −78° C. under N2 flow, lithium diisopropylamine (0.0513 mol, 2 M) was added dropwise. The mixture was allowed to warm to 0° C. and was stirred for 1 hour and then cooled to −78° C. Then iodomethane (0.0582 mol) was added and the reaction mixture was allowed to warm to room temperature and was stirred for 16 hours. A saturated NH4Cl-solution was added and the mixture was extracted with ethyl acetate. The separated organic layer was dried, filtered and the solvent was evaporated. The residue was purified by short open column chromatography over silica gel (eluent: hexane/ethyl acetate 80/20). The product fractions were collected and the solvent was evaporated, yielding 5.91 g of 2-chloro-N-methyl-3-pyridinamine (intermediate 28).

1. temperaturecooled to −78° C
2. temperatureto warm to room temperature
3. stirringwas stirred for 16 hours
4. extractionthe mixture was extracted with ethyl acetate
5. customThe separated organic layer was dried
6. filtrationfiltered
7. customthe solvent was evaporated
8. customThe residue was purified by short open column chromatography over silica gel (eluent: hexane/ethyl acetate 80/20)
9. customThe product fractions were collected
10. customthe solvent was evaporated

ORD record

ord-f2532a0bdbb646dd95616279880e1369

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07081453B2