2-[4-(Aminomethyl)phenyl]benzonitrile → 5-Chloro-7-[(2'-cyanobiphenyl-4-yl)methylamino]pyrazolo[1,5-a]pyrimidine

HRID 1450409Notes

Reaction equation

HRID 1450409 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1.[NH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]#[N:27])=[CH:16][CH:15]=1>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]#[N:27])=[CH:18][CH:19]=2)[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1

Participants

4

Reactant 2

HCID 13933412-[4-(Aminomethyl)phenyl]benzonitrileHCID 110741545,7-Dichloropyrazolo[1,5-a]pyrimidine

Product 1

HCID 105946515-Chloro-7-[(2'-cyanobiphenyl-4-yl)methylamino]pyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.7 g (30.3 mmol) 5,7-dichloropyrazolo[1,5-a]pyrimidine (prepared according to T. Novinson, B. Bhooshan, T. Okabe, G. R. Revankar, R. K. Robins, K. Senga, H. R. Wilson, J. Med. Chem. 1976, 19, 512) and 6.3 g (30.25 mmol) 4-aminomethyl-2'-cyanobiphenyl were dissolved in 150 ml dry ethanol and heated with reflux for 10 h. The solvent was removed in vacuo, the residue dissolved in ethyl acetate, washed with 10% aqueous sodium carbonate solution, and dried over sodium sulfate. After evaporation in vacuo the title compound crystallized from ethyl acetate/ether in colorless crystals,

Workup

  1. temperatureheated
  2. temperaturewith reflux for 10 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwashed with 10% aqueous sodium carbonate solution
  6. dry with materialdried over sodium sulfate
  7. customAfter evaporation in vacuo the title compound
  8. customcrystallized from ethyl acetate/ether in colorless crystals

Sources & evidence

ORD record
ord-7ea937dbef84409a96dcf569ee4f5128
Source dataset
uspto-grants-1997_02
Patent number
US05602136

Reaction notes

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