Ammonium Hydroxide → 4-Iodo-6-methoxypyridin-2-amine

Temperature

120 °C

To a solution of 2-fluoro-4-iodo-6-methoxypyridine (7.1 g, 28 mmol) in n-butanol (64 ml) was added 28% solution of ammonium hydroxide (20 ml, 140 mmol). The reaction mixture was heated to 120° C. After 16 hours LRMS indicated incomplete conversion to product. Additional 28% solution of ammonium hydroxide (20 ml, 140 mmol) was added and the reaction mixture was reheated to 120° C. After 16 h LRMS indicated incomplete conversion to product. Additional 28% solution of ammonium hydroxide (8.0 ml, 56 mmol) was added and the reaction mixture was reheated to 120° C. After 24 h the reaction mixture was cooled, partially concentrated, diluted with ethyl ether, washed with water, then dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (ethyl ether/isohexane gradient) to give 4-iodo-6-methoxypyridin-2-amine LRMS (ESI) calculated for C6H8IN2O [M+H]+, 251.0 found 250.9.

1. customwas reheated to 120° C
2. waitAfter 16 h LRMS indicated incomplete conversion to product
3. customwas reheated to 120° C
4. temperatureAfter 24 h the reaction mixture was cooled
5. concentrationpartially concentrated
6. additiondiluted with ethyl ether
7. washwashed with water
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified by column chromatography on silica gel (ethyl ether/isohexane gradient)

ORD record

ord-b22167b834ff4131999638bf330d5d54

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455477B2