Pyridine → 2-(4-Fluorophenyl)-5-oxo-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

HRID 54946Notes

Reaction equation

HRID 54946 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[C:3]=1[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.[C:20](OC)(=[O:23])[CH:21]=[CH2:22].N1C=CC=CC=1>O>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C:4]2[C:3]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[C:2]3[NH:1][C:20](=[O:23])[CH2:21][CH2:22][N:6]3[N:5]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7294Methyl AcrylateHCID 178509109HCID 178509109, compound

Product 1

HCID 1361791792-(4-Fluorophenyl)-5-oxo-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-amino-3-(4-fluorophenyl)-4-(pyridin-4-yl)pyrazole (1.016 g), methyl acrylate (10 ml), pyridine (20 ml) and water (5 ml) was refluxed for 8 hours. The mixture was cooled and concentrated in vacuo. The residue was dissolved in a mixture of acetic acid (10 ml) and concentrated hydrochloric acid (1.5 ml). The solution was refluxed for 2 hours, cooled and neutralized with an aqueous saturated sodium bicarbonate solution. The separated solid was collected, washed with water and dried to give 2-(4-fluorophenyl)-5-oxo-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (750 mg).

Workup

  1. temperaturewas refluxed for 8 hours
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in a mixture of acetic acid (10 ml) and concentrated hydrochloric acid (1.5 ml)
  5. temperatureThe solution was refluxed for 2 hours
  6. temperaturecooled
  7. customThe separated solid was collected
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-dd01f07c44a84993bf43d21351f9b531
Source dataset
uspto-grants-1997_04
Patent number
US05624931

Reaction notes

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