Ethanol → 5-(4-ethylphenoxy)pyrimidin-4(3H)-one

HRID 1370283Notes

Reaction equation

HRID 1370283 reaction equation
[CH2:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[C:9](=[O:15])[NH:10][C:11](S)=[N:12][CH:13]=2)=[CH:5][CH:4]=1)[CH3:2].C(O)C>C(OCC)(=O)C.ClCCl.[Ni]>[CH2:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[C:9](=[O:15])[NH:10][CH:11]=[N:12][CH:13]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 2

HCID 702EthanolHCID 178436645HCID 178436645, compound

Product 1

HCID 120878165-(4-ethylphenoxy)pyrimidin-4(3H)-oneYield 63%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
40 °C

Procedure

A mixture of 5-(4-ethylphenoxy)-2-(mercapto)pyrimidine-4(3H)-one (2.49 g, 10.28 mmoles), ethanol (250 mL) and wet Raney Ni (50% slurry in water, active catalyst) (Aldrich) (10.9 g) was refluxed with stirring for 3 hours. The reaction was cooled to about 40° C. and filtered through a pad of Celite 545 (Fisher). The pad was washed with hot ethanol (2×75 mL), and the pad was placed in a beaker of water. The combined filtrates were spin evaporated in vacuo to a syrup. The syrup was dissolved in ethyl acetate and reevaporated to give a gray solid. The solid was dissolved in ethyl acetate (40 mL) and applied to a column (4.2×9.5.cm) of Silica Gel 60 (E.M. Science, 230-440 mesh) that was equilibrated with ethyl acetate. The column was eluted with ethyl acetate by flash chromatography, and twelve 100 mL fractions were collected. Fractions 4-10 were combined and spin evaporated in vacuo. The residual oil was dissolved in ethyl acetate and evaporated to give a mixture of light green and white crystals. The crystals were dissolved in dichloromethane and spin evaporated in vacuo to give 1.37 g (63% yield) of 5-(4-ethylphenoxy)pyrimidine-4(3H)-one. Recrystallization of a sample form ethyl acetate gave analytically pure 5-(4-ethylphenoxy)-2-(mercapto)pyrimidine-4(3H)-one as white needles, mp 144-146° C.

Workup

  1. temperaturewas refluxed
  2. filtrationfiltered through a pad of Celite 545 (Fisher)
  3. washThe pad was washed with hot ethanol (2×75 mL)
  4. customThe combined filtrates were spin evaporated in vacuo to a syrup
  5. dissolutionThe syrup was dissolved in ethyl acetate
  6. customreevaporated
  7. customto give a gray solid
  8. washThe column was eluted with ethyl acetate by flash chromatography, and twelve 100 mL fractions
  9. customwere collected
  10. customspin evaporated in vacuo
  11. dissolutionThe residual oil was dissolved in ethyl acetate
  12. customevaporated
  13. customto give
  14. additiona mixture of light green and white crystals
  15. customspin evaporated in vacuo

Sources & evidence

ORD record
ord-1a5bc4a0b5c5454a8fc9190ad5c37471
Source dataset
uspto-grants-2003_06
Patent number
US06583148B1

Reaction notes

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