Ethanol → 2-Furanyl(7-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methanone

HRID 1247964Notes

Reaction equation

HRID 1247964 reaction equation
[NH2:1][C:2]1[C:6]([C:7]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)=[O:8])=[CH:5][NH:4][N:3]=1.[CH2:14](O)[CH3:15]>B(F)(F)F.CCOCC>[O:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:7]([C:6]1[CH:5]=[N:4][N:3]2[C:13]([C:15]3[CH:14]=[CH:9][CH:7]=[CH:6][CH:5]=3)=[CH:12][CH:11]=[N:1][C:2]=12)=[O:8]

Participants

4

Reactant 2

HCID 702EthanolHCID 178509268HCID 178509268, compound

Product 1

HCID 134759012-Furanyl(7-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methanone

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateCatalyst

Procedure

A mixture of 0.86 g of (3-amino-1H-pyrazol-4-yl)-2-furanylmethanone and 0.63 g of 1-phenyl-1-propynone in 35 ml of ethanol with several drops of boron trifluoride etherate was refluxed for 18 hours. The solvent was removed and the residue chromatographed on silica gel with ethyl acetate:hexane (1:20) as eluent and a gradual change to ethyl acetate:hexane (2:5). Elution with ethyl acetate gave a solid which was recrystallized from dichloromethanehexane, giving the desired product, mp 185°-187° C.

Workup

  1. temperaturewas refluxed for 18 hours
  2. customThe solvent was removed
  3. customthe residue chromatographed on silica gel with ethyl acetate:hexane (1:20) as eluent
  4. washElution with ethyl acetate
  5. customgave a solid which
  6. customwas recrystallized from dichloromethanehexane

Sources & evidence

ORD record
ord-14df1ce0d4b049c5bfa939f3ec9fb66c
Source dataset
uspto-grants-1985_06
Patent number
US04521422

Reaction notes

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