Water → 7-(4-chlorophenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

Temperature

60 °C

To a stirred suspension of 7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one (738 mg, 3.0 mmol) in DMF (5 mL) at room temperature under argon was added 5-(chloromethyl)-2-(trifluoromethyl)pyridine (647 mg, 3.3 mmol), followed by K2CO3 (828 mg, 6.0 mmol). The resulting mixture was heated at 60° C. for 48 h, after which time analysis by HPLC/MS indicated that the reaction was complete. After cooling the reaction mixture to room temperature, water (50 mL) was added. The resulting mixture was extracted with EtOAc (2×25 mL). The combined organic layers were washed with saturated aqueous NaCl, then dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting residue was triturated with chloroform (3×20 mL) and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography eluted with ethyl acetate-dichloromethane to obtain 206 mg of the title compound as a solid. HPLC/MS (methanol-water with 10 mM NH4OAc): retention time=3.58 min, [M+H]30 =406.

1. temperatureAfter cooling the reaction mixture to room temperature
2. extractionThe resulting mixture was extracted with EtOAc (2×25 mL)
3. washThe combined organic layers were washed with saturated aqueous NaCl
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. customevaporated under reduced pressure
7. customThe resulting residue was triturated with chloroform (3×20 mL)
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure
10. custompurified by column chromatography
11. washeluted with ethyl acetate-dichloromethane

ORD record

ord-3dc65274179c4b4890f06896b7a87cd0

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07452892B2