Reacción #169716

Ecuación de reacción

4-chloro-5-nitropyrimidine

benzene-1,4-diamine

→

N-(5-nitropyrimidin-4-yl)benzene-1,4-diamine

Rendimiento 47.3%

Disolventes

water

N-methylpyrrolidone

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate (3×50 mL)
2. 2
   LavadoThe combined organic layers were washed with saturated sodium bicarbonate (50 mL)
3. 3
   Secadobrine (50 mL), dried over sodium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónthe filtrate was concentrated under reduced pressure
6. 6
   OtroThe residue obtained
7. 7
   Otrowas purified by chromatography (silica, methylene chloride to 3:97 methanol/methylene chloride)

Procedimiento

A mixture of 4-chloro-5-nitropyrimidine (380 mg) and benzene-1,4-diamine (257 mg) in N-methylpyrrolidone (5 mL) was stirred overnight at ambient temperature. After this time, the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with saturated sodium bicarbonate (50 mL) then brine (50 mL), dried over sodium sulfate, and filtered and the filtrate was concentrated under reduced pressure. The residue obtained was purified by chromatography (silica, methylene chloride to 3:97 methanol/methylene chloride) to afford N-(5-nitropyrimidin-4-yl)benzene-1,4-diamine (260 mg) as a brown oil.

Fuente