3-(3,4-Dichlorophenyl)-3-oxopropanenitrile → 7-Amino-5-(3,4-dichloro-phenyl)-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid

HRID 11881Notes

Reaction equation

HRID 11881 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH2:10][C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:14][C:15]1[NH:19][N:18]=[C:17]([C:20]([OH:22])=[O:21])[CH:16]=1>N1C=CC=CC=1>[NH2:12][C:11]1[N:19]2[N:18]=[C:17]([C:20]([OH:22])=[O:21])[CH:16]=[C:15]2[N:14]=[C:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 27580633-(3,4-Dichlorophenyl)-3-oxopropanenitrileHCID 178418848HCID 178418848, compound

Product 1

HCID 121332247-Amino-5-(3,4-dichloro-phenyl)-pyrazolo[1,5-a]pyrimidine-2-carboxylic acidYield 8.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-(3,4-Dichloro-phenyl)-3-oxo-propionitrile (1.00 g, 4.67 mmol) and 5-amino-1H-pyrazole-3-carboxylic acid (0.593 g, 4.67 mmol) in pyridine (50 mL) was heated at reflux for 3 days. The reaction was concentrated under reduced pressure and the crude product was purified by column chromatography on silica gel to give 7-amino-5-(3,4-dichloro-phenyl)-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (0.125 g, 8%).

Workup

  1. temperatureat reflux for 3 days
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customthe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ce58d50a47684e479766e3f10e08080e
Source dataset
uspto-grants-2006_08
Patent number
US07098335B2

Reaction notes

Loading…