Mesityl oxide → 6,7-Dihydro-2-(4-fluorophenyl)-3-(pyridin-4-yl)-5,7,7-trimethylpyrazolo[1,5-a]pyrimidine

HRID 54956

Reaction equation

HRID 54956 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.[CH3:20][C:21]([CH3:26])=[CH:22][C:23](=O)[CH3:24]>>[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[N:1]=[C:23]([CH3:24])[CH2:22][C:21]([CH3:26])([CH3:20])[N:6]3[N:5]=2)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 8858Mesityl oxideHCID 178509109HCID 178509109, compound

Product 1

HCID 199572396,7-Dihydro-2-(4-fluorophenyl)-3-(pyridin-4-yl)-5,7,7-trimethylpyrazolo[1,5-a]pyrimidine

Procedure

A mixture of 5-amino-3-(4-fluorophenyl)-4-(pyridin-4-yl)pyrazole (254 mg) and 4-methyl-3-penten-2-one (5 ml) was refluxed for 5 hours. The reaction mixture was cooled and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from a mixture of ethyl acetate and hexane to give 6,7-dihydro-2-(4-fluorophenyl)-3-(pyridin-4-yl)-5,7,7-trimethylpyrazolo[1,5-a]pyrimidine (83 mg).

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel
  5. customthe obtained oil was crystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-5245f4db94ff45ddaff1401dd3915f96
Source dataset
uspto-grants-1997_04
Patent number
US05624931

Linked notes

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