Acetone → HCID 86731354, compound

Temperature

70 °C

To a solution of (6-chloro-5-(cyclopropylmethoxy)pyridin-2-yl)methanol (14.0 g) in acetone (100 mL) was added dropwise a solution of potassium permanganate (14.5 g) in water (100 mL) over 40 min at 0° C., and the mixture was stirred at the same temperature for 20 min. The reaction mixture was acidified with 6N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was dissolved in DMF (100 mL), potassium carbonate (9.06 g) and methyl iodide (4.10 mL) were added thereto, and the mixture was stirred with heating at 70° C. for 20 min. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (7.27 g).

1. extractionthe mixture was extracted with ethyl acetate
2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
3. customthe solvent was evaporated under reduced pressure
4. dissolutionThe residue was dissolved in DMF (100 mL)
5. additionpotassium carbonate (9.06 g) and methyl iodide (4.10 mL) were added
6. stirringthe mixture was stirred
7. additionThe reaction mixture was diluted with ethyl acetate
8. washwashed with saturated brine
9. dry with materialdried over anhydrous magnesium sulfate
10. customThe solvent was evaporated under reduced pressure
11. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-50ccc4f552ab404da8945d993406fcbb

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133129B2