Dimethylformamide → 2-Chloro-N-(2-methylpropyl)-6-methyl-3-nitropyridin-4-amine

Temperature

0 °C

2,4-Dichloro-6-methyl-3-nitropyridine (7.01 g), anhydrous dimethylformamide (70 ml), and triethylamine (4.72 ml) were combined and cooled to 0° C. 2-Methylpropylamine (3.36 ml) was added dropwise to the resulting mixture. The reaction was stalled at 75% completion, as determined by HPLC and TLC monitoring, after 16 hours. The dimethylfornamide was removed from the resulting reaction mixture under reduced pressure, and the resulting oil was dissolved in ethyl acetate. The ethyl acetate solution was washed with water, dried with magnesium sulfate, and the solvent was removed under reduced pressure. The resulting yellow oil was put through a column of silica using 90/10 hexane/ethyl acetate. After removing the solvent from the resulting eluted solution, the resulting yellow oil (5.0 g) was dried under high vacuum and used in the next step.

1. customThe dimethylfornamide was removed from the resulting reaction mixture under reduced pressure
2. dissolutionthe resulting oil was dissolved in ethyl acetate
3. washThe ethyl acetate solution was washed with water
4. dry with materialdried with magnesium sulfate
5. customthe solvent was removed under reduced pressure
6. customAfter removing the solvent from the resulting
7. washeluted solution
8. dry with materialthe resulting yellow oil (5.0 g) was dried under high vacuum

ORD record

ord-85147d6c0966467cbefaeb37d65b32cb

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06743920B2