3-(1-Pyrrolidinyl)crotonophenone → 2,5-Dimethyl-7-phenylpyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 1681139Notes

Reaction equation

HRID 1681139 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH3:7])[C:3]=1[C:8]#[N:9].N1(/[C:15](/[CH3:25])=[CH:16]\[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=O)CCCC1>C(O)(=O)C>[CH3:7][C:4]1[C:3]([C:8]#[N:9])=[C:2]2[N:1]=[C:15]([CH3:25])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:6]2[N:5]=1

Participants

4

Reactant 2

HCID 107038983-(1-Pyrrolidinyl)crotonophenoneHCID 178434678HCID 178434678, compound

Product 1

HCID 7547542,5-Dimethyl-7-phenylpyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 78.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4.88 g of 5-amino-3-methyl-4-pyrazolecarbonitrile and 8.61 g of 3-(1-pyrrolidinyl)crotonophenone in 50 ml of glacial acetic acid is stirred and heated at reflux for 6 hours. The reaction mixture is cooled and the procedure described in Example 2 is then followed to obtain 7.77 g of the desired product, mp 175°-177° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. temperatureThe reaction mixture is cooled

Sources & evidence

ORD record
ord-454410fdc4ff48a789946e33232b26fb
Source dataset
uspto-grants-1992_12
Patent number
US05169850

Reaction notes

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