3-amino-5-methyl-1H-pyrazole-4-carbonitrile → 7-(2,5-Dichlorophenyl)-2-methylpyrazolo(1,5-a)pyrimidine-3-carbonitrile

HRID 231499

Reaction equation

HRID 231499 reaction equation
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([CH3:9])[NH:4][N:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[C:18](=O)[CH:19]=[CH:20]N(C)C>C(O)(=O)C>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[C:18]1[N:3]2[N:4]=[C:5]([CH3:9])[C:6]([C:7]#[N:8])=[C:2]2[N:1]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 2274603-amino-5-methyl-1H-pyrazole-4-carbonitrileHCID 28062062',5'-Dichloro-3-dimethylaminoacrylophenone

Product 1

HCID 198072157-(2,5-Dichlorophenyl)-2-methylpyrazolo(1,5-a)pyrimidine-3-carbonitrileYield 70.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 12.2 g of 3-amino-4-cyano-5-methylpyrazole and 24.4 g of 2',5'-dichloro-3-dimethylaminoacrylophenone in 250 ml of glacial acetic acid was heated on a steam bath for 4 hours. The mixture was cooled and filtered and gave 21.28 g of 7-(2,5-dichlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile as off-white crystals.

Workup

  1. temperaturewas heated on a steam bath for 4 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-028806ab420143fdbfad7c38e3b4ba60
Source dataset
uspto-grants-1989_07
Patent number
US04847256

Linked notes

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