2-Propen-1-one, 3-(dimethylamino)-1-(4-pyridinyl)- → 2-(4-Phenylmethyl-1-piperazinyl)-7-(4-pyridyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 482871

Reaction equation

HRID 482871 reaction equation
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)[NH:4][N:3]=1.CN(C)[CH:24]=[CH:25][C:26]([C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)=O>C(O)(=O)C>[C:16]1([CH2:15][N:12]2[CH2:13][CH2:14][N:9]([C:5]3[C:6]([C:7]#[N:8])=[C:2]4[N:1]=[CH:24][CH:25]=[C:26]([C:28]5[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=5)[N:3]4[N:4]=3)[CH2:10][CH2:11]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7145312-Propen-1-one, 3-(dimethylamino)-1-(4-pyridinyl)-HCID 1785104933-Amino-5-(4-benzyl-1-piperazinyl)-4-pyrazolecarbonitrile

Product 1

HCID 135799502-(4-Phenylmethyl-1-piperazinyl)-7-(4-pyridyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 53.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2.2 g of 3-amino-5-(4-phenylmethyl-1-piperazinyl)-4-pyrazolecarbonitrile (Example 1) and 1.37 g of 3-dimethylamino-1-(4-pyridyl)-2-propen-1-one U.S. Pat. No. 4,281,000, Example 63) in 25 ml of glacial acetic acid was refluxed for 6 hours. The solution was taken to dryness in vacuo. The residue was partitioned between saturated sodium bicarbonate and dichloromethane (1:2). The dichloromethane layer was separated, dried over anhydrous sodium sulfate and filtered through a short column of magnesium silicate. The effluent was refluxed on a steam bath with the gradual addition of hexane until turbidity was noted. After cooling, the precipitate was collected by filtration. The solid was recrystallized from dichloromethane/hexane and gave 1.65 g of the product of the Example as very pale yellow crystals, mp 193°-194° C.

Workup

  1. customThe residue was partitioned between saturated sodium bicarbonate and dichloromethane (1:2)
  2. customThe dichloromethane layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered through a short column of magnesium silicate
  5. temperatureThe effluent was refluxed on a steam bath with the gradual addition of hexane until turbidity
  6. temperatureAfter cooling
  7. filtrationthe precipitate was collected by filtration
  8. customThe solid was recrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-056c2d11bb104294950d660e900b5b77
Source dataset
uspto-grants-1986_03
Patent number
US04576943

Linked notes

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