Ethyl formate → 4,5-Dihydro-3-(4-fluorophenyl)-5-oxo-2-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine

HRID 54944Notes

Reaction equation

HRID 54944 reaction equation
[Na].C([O:5][CH2:6][CH3:7])(=O)C.[CH:8](OCC)=O.[NH2:13][C:14]1[NH:18][N:17]=[C:16]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[C:15]=1[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1>C1(C)C=CC=CC=1.C(O)C>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:15]2[C:16]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[N:17][N:18]3[CH:8]=[CH:7][C:6](=[O:5])[NH:13][C:14]=23)=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 8025Ethyl formateHCID 8857Ethyl AcetateHCID 5360545SodiumHCID 178509114HCID 178509114, compound

Product 1

HCID 1363784164,5-Dihydro-3-(4-fluorophenyl)-5-oxo-2-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of sodium (28 mg), ethyl acetate (0.12 ml) and ethyl formate (0.10 ml) in dry toluene (0.5 ml) was stirred at ambient temperature for 14 hours under nitrogen. To the mixture was added 5-amino-4-(4-fluorophenyl)-3-(pyridin-4-yl)pyrazole (150 mg) in dry ethanol (1.5 ml) and the mixture was refluxed for 7 hours. The reaction mixture was cooled and the separated solid was collected and dried. The solid was dissolved in water (15 ml) and the solution was washed with ether. The aqueous solution was neutralized with diluted hydrochloric acid. The separated solid was collected, washed with water and dried to give 4,5-dihydro-3-(4-fluorophenyl)-5-oxo-2-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine (62 mg).

Workup

  1. temperaturethe mixture was refluxed for 7 hours
  2. temperatureThe reaction mixture was cooled
  3. customthe separated solid was collected
  4. customdried
  5. dissolutionThe solid was dissolved in water (15 ml)
  6. washthe solution was washed with ether
  7. customThe separated solid was collected
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-eb270a8570bd4b7dac4e67f463e51d21
Source dataset
uspto-grants-1997_04
Patent number
US05624931

Reaction notes

Loading…