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

HRID 1450399Notes

Reaction equation

HRID 1450399 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH3:11])[CH: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>[C:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:17]1[CH:16]=[CH:15][C:14]([CH2:13][NH:12][C:2]2[N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=[C:4]([CH3:11])[CH:3]=2)=[CH:19][CH:18]=1)#[N:27]

Participants

4

Reactant 2

HCID 13933412-[4-(Aminomethyl)phenyl]benzonitrileHCID 104872877-Chloro-5-methylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 104972947-[(2'-Cyanobiphenyl-4-yl)methylamino]-5-methylpyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.35 g (20 mmol) 7-chloro-5-methylpyrazolo[1,5-a]pyrimidine (prepared according to Y. Makisumi, Chem. Pharm. Bull. 1962, 10, 620) and 4.17 g (20 mmol) 4-aminomethyl-2'-cyanobiphenyl were heated with reflux in 40 ml dry ethanol for 4 hours. The solvent was distilled off in vacuo, and the remaining oil solidified after stirring with a mixture of 20 ml hexane and 20 ml t-butylmethylether to give a reddish powder of the pure title compound,

Workup

  1. distillationThe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-20b86fc3cdc44b39ac3c0b535df5ddef
Source dataset
uspto-grants-1997_02
Patent number
US05602136

Reaction notes

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