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2(1H)-Pyrimidinone → HCID 22490955、化合物

HRID 2180557
ノート
印刷プレビュー

反応式

HRID 2180557 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 684012(1H)-PyrimidinoneHCID 22490916HCID 22490916、化合物HCID 178418586HCID 178418586、化合物

生成物 1

HCID 22490955HCID 22490955、化合物

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-a66c0c830b6145a9bd95d10b73f9a810
出典データセット
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06887896B1

反応ノート

読み込み中…

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