Hydrochloric Acid → HCID 14480891, compound

Temperature

130 °C

To 4-chloro-6-methylpyridin-2-amine (1.0 g, 7.0 mmol) was added sodium methoxide (25% solution in methanol, 9.2 ml, 35 mmol) under a nitrogen atmosphere. The reaction mixture was heated in a microwave at 130° C. for 12 hours. The reaction mixture was quenched with hydrochloric acid (1.0 M in water, 42 ml, 42 mmol), and the reaction mixture was partially concentrated under reduced pressure to remove methanol. The residue was diluted with ethyl acetate, and the pH was adjusted to ˜7.5 with saturated aqueous sodium bicarbonate solution. The organics were separated, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (dichloromethane/methanol with ammonium hydroxide, linear gradient) to afford 4-methoxy-6-methylpyridin-2-amine. MS ESI calc'd. for C7H11N2O [M+H]+ 139. found 139. 1H NMR (500 MHz, DMSO-d6) δ 5.96 (d, J=1.5 Hz, 1H), 5.75 (d, J=2.0 Hz, 1H), 5.70 (br s, 2H), 3.66 (s, 3H), 2.13 (s, 3H).

1. concentrationthe reaction mixture was partially concentrated under reduced pressure
2. customto remove methanol
3. additionThe residue was diluted with ethyl acetate
4. customThe organics were separated
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel chromatography (dichloromethane/methanol with ammonium hydroxide, linear gradient)

ORD record

ord-d451faf9acf24e2b80ab1c65b2f460ad

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216173B2