2(1H)-Pyrimidinone → HCID 22490955, compound

HRID 2180557Notes

Reaction equation

HRID 2180557 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][CH2:8][C:9]2=O)=[CH:4][C:3]=1[O:15][CH2:16][CH3:17].N1C=CC=NC1=O.[C:25]([Mg]Br)([CH3:28])([CH3:27])[CH3:26]>C1COCC1.CCOCC>[Br:1][C:2]1[CH:11]=[C:10]2[C:5](=[CH:4][C:3]=1[O:15][CH2:16][CH3:17])[C:6]([CH3:14])([CH3:13])[CH2:7][CH:8]=[C:9]2[C:25]([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 684012(1H)-PyrimidinoneHCID 22490916HCID 22490916, compoundHCID 178418586HCID 178418586, compound

Product 1

HCID 22490955HCID 22490955, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 7-bromo-6-ethoxy-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one (Compound A-4, 2.0 g, 6.73 mmol) in THF (20 mL), ether (20 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1])-pyrimidinone (8 mL) at −30° C. was added a solution of tert-butylmagnesium bromide (2M in ether, 13.5 mL, 27 mmol). The reaction was allowed to warm to room temperature over 5 h. The reaction was quenched with ice water and extracted with ether. The organic layer was washed successively with water, brine, dried over Na2SO4, and concentrated in vacuo. The crude material was then dissolved in methanol (20 mL). After catalytic amount of p-toluenesulfonic acid was added, the reaction was stirred at 50° C. for 2 h. The solvent was removed in vacuo. The residue was purified by column chromatography (silica gel, 1% ethyl acetate in hexane) to afford the title compound as a pale yellow oil

Workup

  1. customThe reaction was quenched with ice water
  2. extractionextracted with ether
  3. washThe organic layer was washed successively with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude material was then dissolved in methanol (20 mL)
  7. additionAfter catalytic amount of p-toluenesulfonic acid was added
  8. customThe solvent was removed in vacuo
  9. customThe residue was purified by column chromatography (silica gel, 1% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a66c0c830b6145a9bd95d10b73f9a810
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

Loading…