Potassium Carbonate → HCID 23325341, compound

HRID 1380526Notes

Reaction equation

HRID 1380526 reaction equation
[N:1]1([C:7]2[N:21]=[C:10]3[N:11]=[CH:12][CH:13]=[C:14]([C:15]4[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=4)[N:9]3[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:23][CH2:24][CH2:25][C:26]#[N:27].C(=O)([O-])[O-].[K+].[K+].[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2]>C(Cl)(Cl)Cl.CN(C)C=O>[N:18]1[CH:19]=[CH:20][C:15]([C:14]2[N:9]3[N:8]=[C:7]([N:1]4[CH2:2][CH2:3][N:4]([CH2:23][CH2:24][CH2:25][C:26]#[N:27])[CH2:5][CH2:6]4)[N:21]=[C:10]3[N:11]=[CH:12][CH:13]=2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 66225Magnesium orthosilicateHCID 13686022HCID 13686022, compound

Product 1

HCID 23325341HCID 23325341, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.6 g (0.02 moles) of 2-(1-piperazinyl)-7-(4-pyridyl)[1,2,4]triazolo[1,5-a]pyrimidine (prepared as described in Example 47), 3.0 g (0.02 moles) of 4-bromobutyronitrile, 4.0 g of potassium carbonate and 50 ml of N,N-dimethylformamide was heated at reflux for 16 hours with stirring. The mixture was cooled and filtered. The filter was washed with N,N-dimethylformamide and the combined filtrate and wash was evaporated in vacuo to give a dark syrup. The syrup was dissolved in chloroform and passed through a pad of magnesium silicate washing with chloroform. The filtrate was evaporated to a syrup and crystallized from ethanol/ether. The precipitate was collected by filtration and washed with ether and gave 2.1 g of the desired product as golden crystals, mp 147°-148° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washThe filter was washed with N,N-dimethylformamide
  6. washthe combined filtrate and wash
  7. customwas evaporated in vacuo
  8. customto give a dark syrup
  9. customThe filtrate was evaporated to a syrup
  10. customcrystallized from ethanol/ether
  11. filtrationThe precipitate was collected by filtration
  12. washwashed with ether

Sources & evidence

ORD record
ord-3754cd183b8e4ce6bd08d089d3970db3
Source dataset
uspto-grants-1986_04
Patent number
US04582833

Reaction notes

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