HCID 23447583, compound → HCID 22000251, compound

HRID 1976150Notes

Reaction equation

HRID 1976150 reaction equation
[CH2:1]1O[C:4]2([CH2:9][CH2:8][N:7]([C:10]3[CH:15]=[C:14](Cl)[N:13]=[CH:12][N:11]=3)[CH2:6][CH2:5]2)[O:3][CH2:2]1>C(O)C.C(OCC)(=O)C.[Pd]>[CH2:1]=[CH2:2].[N:13]1[CH:14]=[CH:15][C:10]([N:7]2[CH2:6][CH2:5][C:4](=[O:3])[CH2:9][CH2:8]2)=[N:11][CH:12]=1

Participants

5

Reactant 1

HCID 23447583HCID 23447583, compound

Product 1

HCID 22000251HCID 22000251, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(6-chloropyrimidin-4-yl)-4-piperidone ethylene ketal (2 g, 8.87 mmol) in ethanol (25 ml) and ethyl acetate (25 ml) was hydrogenated at 60 psi for 1 hr over 10% Pd/C (0.25 g). The mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in methylene chloride and filtered through celite. The filtrate was concentrated in vacuo to give 1-(pyrimidin-4-yl)-4-piperidone ethylene as a white solid (112-115° C.).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in methylene chloride
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-50ed8ee3bf06437e9ace5b720dd8043f
Source dataset
uspto-grants-2001_05
Patent number
US06225324B1

Reaction notes

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