Ethanol → 5-Methoxy-2-(4-hydroxyphenyl)pyrimidine

HRID 485990Notes

Reaction equation

HRID 485990 reaction equation
[H][H].Cl[C:4]1[C:9]([O:10][CH3:11])=[C:8](Cl)[N:7]=[C:6]([C:13]2[CH:18]=[CH:17][C:16]([O:19]CC3C=CC=CC=3)=[CH:15][CH:14]=2)[N:5]=1.C(N(CC)CC)C.C(O)C>[Pd].O>[CH3:11][O:10][C:9]1[CH:8]=[N:7][C:6]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[N:5][CH:4]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 190970644,6-Dichloro-5-methoxy-2-(4-benzyloxyphenyl)pyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 1357369415-Methoxy-2-(4-hydroxyphenyl)pyrimidineYield 90.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Hydrogen gas was blown into a mixture of 21 g of 4,6-dichloro-5-methoxy-2-(4-benzyloxyphenyl)pyrimidine, 18.1 g of triethylamine, 3.15 g of 10% palladium-on-carbon, 210 ml of ethanol, and 11 ml of water, followed by stirring at 40° C. for 6 hours. The catalyst was removed by filtration, and the filtrate was poured into 300 ml of water and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and distilled to remove ethyl acetate to afford 8.93 g (percent yield: 90.9%) of 5-methoxy-2-(4-hydroxyphenyl)pyrimidine.

Workup

  1. customThe catalyst was removed by filtration
  2. additionthe filtrate was poured into 300 ml of water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationdistilled
  6. customto remove ethyl acetate

Sources & evidence

ORD record
ord-0bc80f25355f44b59294d2258f89aebc
Source dataset
uspto-grants-1994_03
Patent number
US05290477

Reaction notes

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