Methane → 2-[4-(5-Hydroxy-1-pentyl)phenyl]-5-(ethoxy)pyrimidine

HRID 1728264Notes

Reaction equation

HRID 1728264 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][N:14]=2)=[CH:9][CH:8]=1.C.[H][H]>[Pd].C(OCC)(=O)C>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][N:14]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 297MethaneHCID 540063702-[4-(5-Hydroxy-1-pentenyl)phenyl]-5-(ethoxy)pyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 190170732-[4-(5-Hydroxy-1-pentyl)phenyl]-5-(ethoxy)pyrimidineYield 70.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 12 g of 2-[4-(5-hydroxy-1-pentenyl)phenyl]-5-(ethoxy)pyrimidine, 2 g of palladium on active charcoal (10 w/w %) and 150 ml of ethyl acetate was hydrogenated at normal pressure and room temperature until one molar equivalent of hydrogen had been taken up. The inorganic material was filtered off and the filtrate was concentrated. The residue was purified by chromatography on silica gel with hexane/ethyl acetate (vol. 8:2). Recrystallization from ethyl alcohol gave 8.5 g of pure 2-[4-(5-hydroxy-1-pentyl)phenyl]-5-(ethoxy)pyrimidine.

Workup

  1. filtrationThe inorganic material was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by chromatography on silica gel with hexane/ethyl acetate (vol. 8:2)
  4. customRecrystallization from ethyl alcohol

Sources & evidence

ORD record
ord-ff325cb2a99b474a898129ff4e785f1c
Source dataset
uspto-grants-1994_07
Patent number
US05326497

Reaction notes

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