Реакция #11449

Уравнение реакции

tert-butyl 4-aminobutylcarbamate

2,4-dichloro-5,6-dimethyl-3-nitropyridine

triethylamine

→

tert-butyl 4-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]butylcarbamate

Выход 48.0%

Растворители

N,N-dimethylformamide

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   Концентрированиеconcentrated under reduced pressure
2. 2
   ДругоеThe residue was partitioned between water and ethyl acetate
3. 3
   ДругоеThe layers were separated
4. 4
   Экстракцияthe aqueous layer was extracted with ethyl acetate
5. 5
   Промывкаwashed with brine
6. 6
   Концентрированиеconcentrated under reduced pressure
7. 7
   Другоеto provide a brown oily residue
8. 8
   ДругоеThis material was purified by flash chromatography (400 mL silica gel
9. 9
   Промывкаeluting initially with 10% ethyl acetate in hexane
10. 10
    Температураincreasing the gradient to 15%

Методика

A solution of tert-butyl 4-aminobutylcarbamate (8.52 g, 45.24 mmol) in N,N-dimethylformamide was added to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (10.00 g, 45.24 mmol) and triethylamine (12.6 mL, 90.5 mmol) in N,N-dimethylformamide (320 mL). The reaction mixture was stirred overnight and then concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organics were combined, washed with brine and then concentrated under reduced pressure to provide a brown oily residue. This material was purified by flash chromatography (400 mL silica gel, eluting initially with 10% ethyl acetate in hexane and then increasing the gradient to 15% and then to 25%) to provide 8.1 g of tert-butyl 4-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]butylcarbamate as a yellow solid.

Источник