Pyridine → 5-chloro-N-(5-(3,4-dimethylphenyl)pyrimidin-2-yl)-2-nitrobenzamide

Into a 250-mL round-bottom flask, was placed a solution of 5-(3,4-dimethylphenyl)pyrimidin-2-amine (1.41 g, 7.07 mmol, 1.00 equiv) in dichloromethane (90 mL), and pyridine (1.73 g, 3.00 equiv). This was followed by dropwise addition of a solution of 5-chloro-2-nitrobenzoyl chloride (1.60 g, 7.27 mmol, 1.00 equiv) in dichloromethane (30 mL) with stirring. The resulting solution was stirred overnight at 25° C. in an oil bath. The resulting solution was diluted with 60 mL of dichloromethane. The resulting mixture was washed with 1×30 mL of hydrogen chloride (aq) and 3×200 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was dissolved in 100 mL of methanol, to this was added potassium carbonate (5.12 g). The mixture was stirred for 3 h at 30° C. The resulting mixture was concentrated under vacuum and dissolved in 100 mL of ethyl acetate. The resulting mixture was washed with 3×50 mL brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was washed with ethyl acetate:n-hexane (30 mL:30 mL). This resulted in 0.78 g (29%) of 5-chloro-N-(5-(3,4-dimethylphenyl)pyrimidin-2-yl)-2-nitrobenzamide as a off-white solid.

1. customInto a 250-mL round-bottom flask, was placed
2. stirringThe resulting solution was stirred overnight at 25° C. in an oil bath
3. washThe resulting mixture was washed with 1×30 mL of hydrogen chloride (aq) and 3×200 mL of brine
4. dry with materialThe mixture was dried over anhydrous sodium sulfate
5. concentrationconcentrated under vacuum
6. dissolutionThe residue was dissolved in 100 mL of methanol
7. additionto this was added potassium carbonate (5.12 g)
8. stirringThe mixture was stirred for 3 h at 30° C
9. concentrationThe resulting mixture was concentrated under vacuum
10. dissolutiondissolved in 100 mL of ethyl acetate
11. washThe resulting mixture was washed with 3×50 mL brine
12. dry with materialThe mixture was dried over anhydrous sodium sulfate
13. concentrationconcentrated under vacuum
14. washThe crude product was washed with ethyl acetate
15. customThis resulted in 0.78 g (29%) of 5-chloro-N-(5-(3,4-dimethylphenyl)pyrimidin-2-yl)-2-nitrobenzamide as a off-white solid

ORD record

ord-7be55e9537d9427c9e081ef7181a71a7

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809339B2