Pyridine → 4-Chloro-N-(4-chloropyrimidin-5-yl)-3-cyanobenzamide

4-Chloro-3-cyanobenzoic acid (7.01 g, 38.6 mmol) was suspended in benzene (70 mL). Thionyl chloride (3.6 mL, 49.6 mmol) was added to the suspension, and the mixture was refluxed with heating for 4 hours. The reaction liquid was condensed under reduced pressure. 5-Amino-4-chloropyrimidine (5.00 g, 38.6 mmol), dichloromethane (70 mL), and pyridine (3.6 mL, 44.5 mmol) were added to the obtained acid chloride. The mixture was stirred at room temperature for 7 hours. Chloroform (50 mL) and water (50 mL) was added to the reaction solution to filtrate crystals. The obtained crystals were washed with chloroform (20 mL) and water (20 mL), and air-dried to obtain 7.35 g (yield: 65%) of the subject compound as white crystals. Further, 0.62 g (yield: 8%) of the subject compound was obtained from a mixed solution of mother liquid and washings as pale brown crystals (secondary crystals). The total yield was 73%.

1. temperaturethe mixture was refluxed
2. temperaturewith heating for 4 hours
3. customThe reaction liquid
4. customcondensed under reduced pressure
5. washThe obtained crystals were washed with chloroform (20 mL) and water (20 mL)
6. customair-dried

ORD record

ord-62a4a92b051e418388ead2567e3ea4a2

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08314085B2