Ammonia → HCID 86630699, compound

Temperature

60 °C

2.00 g methyl 5,7-dichloro-6-phenylpyrazolo[1,5-a]pyrimidine-2-carboxylate were dissolved in 40 mL dichloromethane. 40 mL brine, 20 mL ammonia solution 25% w/w and 1.22 g zinc powder were added and the mixture was stirred at 60° C. for 3 h. The reaction mixture was filtered through Celite and was washed with dichloromethane and water. The organic phase was separated and the water phase was extracted with dichloromethane. The combined dichloromethane phase was dried over Na2SO4 and evaporated. The crude product contained methyl 5,7-dichloro-6-phenylpyrazolo[1,5-a]pyrimidine-2-carboxylate. The crude product was dissolved again in 20 mL dichloromethane. 20 mL brine, 10 mL ammonia solution 25% w/w and 0.60 g zinc powder were added and the mixture was stirred at 60° C. for 45 min. The reaction mixture was filtered through Celite and washed with dichloromethane and water. The organic phase was separated and the water phase was extracted with dichloromethane. The combined dichloromethane phase was dried over Na2SO4, the solvent was evaporated and the residue was purified by chromatography on silica gel (dichloromethane/ethyl acetate) to yield the desired compound.

1. filtrationThe reaction mixture was filtered through Celite
2. washwas washed with dichloromethane and water
3. customThe organic phase was separated
4. extractionthe water phase was extracted with dichloromethane
5. dry with materialThe combined dichloromethane phase was dried over Na2SO4
6. customevaporated
7. dissolutionThe crude product was dissolved again in 20 mL dichloromethane
8. addition20 mL brine, 10 mL ammonia solution 25% w/w and 0.60 g zinc powder were added
9. stirringthe mixture was stirred at 60° C. for 45 min
10. filtrationThe reaction mixture was filtered through Celite
11. washwashed with dichloromethane and water
12. customThe organic phase was separated
13. extractionthe water phase was extracted with dichloromethane
14. dry with materialThe combined dichloromethane phase was dried over Na2SO4
15. customthe solvent was evaporated
16. customthe residue was purified by chromatography on silica gel (dichloromethane/ethyl acetate)

ORD record

ord-0c718bc0bb25462e8cbfc261d7f00dee

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957064B2