4-[3-(Bicyclo[2.2.1]hept-2-yloxy)-4-Methoxyphenyl]-4-Hydroxy-1,2,3,4-Tetrahydro-2-Pyrimidinone → HCID 178488672, compound

HRID 2210487Notes

Reaction equation

HRID 2210487 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[O:8][C:9]1[CH:10]=[C:11]([C:17]2(O)[CH:22]=[CH:21][NH:20][C:19](=[O:23])[NH:18]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]>C(O)C>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[O:8][C:9]1[CH:10]=[C:11]([C:17]2[CH:22]=[CH:21][NH:20][C:19](=[O:23])[N:18]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

Participants

3

Reactant 1

HCID 140101864-[3-(Bicyclo[2.2.1]hept-2-yloxy)-4-Methoxyphenyl]-4-Hydroxy-1,2,3,4-Tetrahydro-2-Pyrimidinone

Product 1

HCID 178488672HCID 178488672, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The hydroxy pyrimidinone of Example 60 (0.2 g, 0.61 mmol) is dissolved in 5 ml ethanol, treated with 2.5 ml 1N HC1 and refluxed for 6 hours. The reaction is cooled to room temperature, quenched with water and the product extracted 3x ethyl acetate. The organics are washed, dried, filtered and concentrated in vacuo to yield a crude substance which is crystallized from ethyl acetate to give 60 mg (31.5%) of the pyrimidinone as a crystalline solid. This material is a 7:3 mixture of endo-exo bicycloalkyl isomers.

Workup

  1. additiontreated with 2.5 ml 1N HC1
  2. temperaturerefluxed for 6 hours
  3. customquenched with water
  4. extractionthe product extracted 3x ethyl acetate
  5. washThe organics are washed
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield a crude substance which
  10. customis crystallized from ethyl acetate

Sources & evidence

ORD record
ord-f7145ebc684043138c3b7daa780d0f6c
Source dataset
uspto-grants-1995_10
Patent number
US05459145

Reaction notes

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