Acetic Acid → 5-Methyl-7-phenyl-2-[4-(phenylmethyl)-1-piperazinyl]-pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 482874Notes

Reaction equation

HRID 482874 reaction equation
[C:1]1([C:7](=O)[CH2:8][C:9](=O)[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C:14]1[C:18]([C:19]#[N:20])=[C:17]([N:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:23][CH2:22]2)[NH:16][N:15]=1.C(O)(=O)C>ClCCl>[CH3:10][C:9]1[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:15]2[N:16]=[C:17]([N:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:23][CH2:22]3)[C:18]([C:19]#[N:20])=[C:14]2[N:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7166BenzoylacetoneHCID 1785104933-Amino-5-(4-benzyl-1-piperazinyl)-4-pyrazolecarbonitrile

Product 1

HCID 135799875-Methyl-7-phenyl-2-[4-(phenylmethyl)-1-piperazinyl]-pyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 74.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.9 g (0.018 moles) of 1-phenyl-1,3-butanedione, 5.0 g (0.018 moles) of 3-amino-5-(4-phenylmethyl-1-piperazinyl)-4-pyrazolecarbonitrile (prepared as described in Example 1) and 25 ml of glacial acetic acid was refluxed for 4 hours. The reaction mixture was evaporated in vacuo and gave a thick oil. The oil was dissolved in dichloromethane and partitioned with saturated sodium bicarbonate. The organic layer was separated, dried over anhydrous sodium sulfate and passed through magnesium silicate. The solution was evaporated in vacuo and gave a yellow solid which was recrystallized from isopropanol and cyclohexane and gave 5.5 g of the desired product as a light yellow solid, mp 160°-164° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. customgave a thick oil
  4. custompartitioned with saturated sodium bicarbonate
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solution was evaporated in vacuo
  8. customgave a yellow solid which
  9. customwas recrystallized from isopropanol and cyclohexane

Sources & evidence

ORD record
ord-d2dbf030d2e94fa3be2b996bab2f0035
Source dataset
uspto-grants-1986_03
Patent number
US04576943

Reaction notes

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