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

HRID 2180557
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HRID 2180557 반응식
[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]
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참가 물질

6

반응물 3

HCID 684012(1H)-PyrimidinoneHCID 22490916HCID 22490916, 화합물HCID 178418586HCID 178418586, 화합물

생성물 1

HCID 22490955HCID 22490955, 화합물

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-a66c0c830b6145a9bd95d10b73f9a810
출처 데이터셋
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06887896B1

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