2-Chlorobenzoxazole → N-1,3-benzoxazol-2-yl-N'-(5-nitropyrimidin-4-yl)benzene-1,4-diamine

A mixture of N-(5-nitropyrimidin-4-yl)benzene-1,4-diamine (256 mg), 2-chloro-1,3-benzoxazole (110 mg) in N-methylpyrrolidone (3 mL) was stirred at 120° C. for 45 min. After this time, the reaction mixture was cooled to ambient temperature, diluted with water (50 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with water (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 1:3 ethyl acetate/methylene chloride) to afford N-1,3-benzoxazol-2-yl-N′-(5-nitropyrimidin-4-yl)benzene-1,4-diamine (107 mg) as a red solid.

1. temperatureAfter this time, the reaction mixture was cooled to ambient temperature
2. extractionextracted with ethyl acetate (100 mL)
3. washThe organic layer was washed with water (50 mL)
4. dry with materialbrine (50 mL), dried over sodium sulfate
5. filtrationfiltered
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe residue obtained
8. customwas purified by chromatography (silica, methylene chloride to 1:3 ethyl acetate/methylene chloride)

ORD record

ord-f75b234560ce471f862fbe733abf6949

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09226921B2