Triethylamine → Tert-butyl 2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]ethylcarbamate

Temperatur

60 °C

A solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (60 g, 271 mmol) in anhydrous N,N-dimethylformamide (600 mL) was cooled to 0° C. Triethylamine (44.8 mL, 326 mmol) was added drop wise followed by tert-butyl 2-aminoethylcarbamate (52.2 g, 326 mmol). After 30 minutes the ice bath was removed and the reaction mixture was heated to 60° C. The reaction was heated at 60° C. overnight and then it was concentrated under reduced pressure to provide an orange oil. The oil was dissolved in ethyl acetate (1 L), washed with water (3×500 mL), dried over magnesium sulfate and then concentrated under reduced pressure to provide a yellow oil. The oil was triturated with methanol (˜100 mL). The resulting solid was isolated by filtration and washed with cold methanol to provide 72.3 g of tert-butyl 2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]ethylcarbamate as a solid.

1. customAfter 30 minutes the ice bath was removed
2. temperatureThe reaction was heated at 60° C. overnight
3. concentrationit was concentrated under reduced pressure
4. customto provide an orange oil
5. washwashed with water (3×500 mL)
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customto provide a yellow oil
9. customThe oil was triturated with methanol (˜100 mL)
10. customThe resulting solid was isolated by filtration
11. washwashed with cold methanol

ORD-Eintrag

ord-93bc3839ace74cb5bd8303c2526063ba

Quelldatensatz

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07098221B2