Reaction #169716

Reaction equation

4-chloro-5-nitropyrimidine

benzene-1,4-diamine

→

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

Yield 47.3%

Solvents

water

N-methylpyrrolidone

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate (3×50 mL)
2. 2
   WashThe combined organic layers were washed with saturated sodium bicarbonate (50 mL)
3. 3
   Dryingbrine (50 mL), dried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationthe filtrate was concentrated under reduced pressure
6. 6
   OtherThe residue obtained
7. 7
   Otherwas purified by chromatography (silica, methylene chloride to 3:97 methanol/methylene chloride)

Procedure

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.

Source