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

HRID 1450370Notes

Reaction equation

HRID 1450370 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-5bfb950aa5064d75b87fbf97324b00ca
Source dataset
uspto-grants-1997_02
Patent number
US05602137

Reaction notes

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