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

HRID 1898891Notes

Reaction equation

HRID 1898891 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH2:11][CH3:12])[CH:3]=1.[NH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]#[N:28])=[CH:17][CH:16]=1>C(O)C>[C:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[CH:17]=[CH:16][C:15]([CH2:14][NH:13][C:2]2[N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=[C:4]([CH2:11][CH3:12])[CH:3]=2)=[CH:20][CH:19]=1)#[N:28]

Participants

4

Reactant 2

HCID 13933412-[4-(Aminomethyl)phenyl]benzonitrileHCID 105354107-Chloro-5-ethylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 105220187-[(2'-Cyanobiphenyl-4-yl)methylamino]-5-ethylpyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.5 g (30.3 mmol) of the chloride from Example 1, Step B and 6.3 g (30.3 mmol) of 4-aminomethyl-2'-cyanobiphenyl (prepared according to EP 459 136) were heated in 150 ml dry ethanol for 10 h. After removal of the solvent in vacuo yellow crystals formed. These were purified by suspension in acetone and dissolved in ethyl acetate. The solution was washed with 10% sodium carbonate solution, the organic layer dried over sodium sulfate, and evaporated to dryness to give colorless crystals of the title compound, m.p. 230°-233° C.

Workup

  1. customAfter removal of the solvent in vacuo yellow crystals
  2. customformed
  3. customThese were purified by suspension in acetone
  4. dissolutiondissolved in ethyl acetate
  5. washThe solution was washed with 10% sodium carbonate solution
  6. dry with materialthe organic layer dried over sodium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-543dcf9616d443eeb84ae19692392c7e
Source dataset
uspto-grants-1996_11
Patent number
US05571813

Reaction notes

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