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

HRID 1247963Notes

Reaction equation

HRID 1247963 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.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17](S(O)(=O)=O)=[CH:16][CH:15]=1.[CH2:25](O)[CH3:26]>>[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:24]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:26][CH:25]=[N:1][C:2]=12)=[O:8]

Participants

4

Reactant 3

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 178509268HCID 178509268, compound

Product 1

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

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 25 ml of ethanol with a catalytic amount of p-toluenesulfonic acid was heated on a steam bath for 1.5 hours. The mixture was chilled and then filtered giving 1.0 g of yellow solid. This solid was dissolved in a small amount of dichloromethane and placed on a silica gel column. The column was eluted with ethyl acetate:hexane (1:20) with a gradual change to ethyl acetate:hexane (2:5) as eluent. The column was then washed with ethyl acetate and the ethyl acetate wash was concentrated to a solid. This solid was cyrstallized from dichloromethane, giving 0.85 g of the desired product as cream crystals having a melting point of 188°-190° C. and a pmr spectrum identical to that of the product prepared as described in Example 22.

Workup

  1. temperaturewas heated on a steam bath for 1.5 hours
  2. temperatureThe mixture was chilled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-9a446121053b42838120bdc8221ad9d8
Source dataset
uspto-grants-1985_06
Patent number
US04521422

Reaction notes

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