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Acetic Acid → 6-(3,4-dimethoxy-phenyl)-8-phenyl-2-phenylamino-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

HRID 11791
ノート
印刷プレビュー

反応式

HRID 11791 の反応式
C([O:3][C:4](=O)[CH:5]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=1)[CH2:6][C:7]1[C:8]([NH:20]C2C=CC=CC=2)=[N:9][C:10]([NH:13]C2C=CC=CC=2)=[N:11][CH:12]=1)C.S(=O)(=O)(O)O.[C:43](O)(=O)[CH3:44]>C(OCC)(=O)C>[CH3:36][O:35][C:29]1[CH:28]=[C:27]([CH:5]2[C:4](=[O:3])[N:20]([C:44]3[CH:43]=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:8]3[N:9]=[C:10]([NH:13][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:11]=[CH:12][C:7]=3[CH2:6]2)[CH:32]=[CH:31][C:30]=1[O:33][CH3:34]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 210443063-(2,4-Diphenylamino-pyrimidin-5-yl)-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester

生成物 1

HCID 100268676-(3,4-dimethoxy-phenyl)-8-phenyl-2-phenylamino-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a solution of 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester (470 mg, 0.94 mmol) (from Example 11b supra) in glacial acetic acid (3 mL) was added concentrated sulfuric acid (0.1 mL) in one portion. The reaction mixture was heated at 80° C. overnight. After cooling, the reaction mixture was diluted with ethyl acetate (50 mL) and quenched with 2 N aqueous sodium hydroxide solution. The organic layer was separated and successively washed with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give the crude product which was crystallized from ethyl acetate-hexanes to give 6-(3,4-dimethoxy-phenyl)-8-phenyl-2-phenylamino-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one as a light brown solid. (Yield 335 mg, 78.8%).

後処理

  1. temperatureAfter cooling
  2. customquenched with 2 N aqueous sodium hydroxide solution
  3. customThe organic layer was separated
  4. washsuccessively washed with water (10 mL) and brine (10 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude product which
  9. customwas crystallized from ethyl acetate-hexanes

出典と根拠

ORDレコード
ord-f879e793117f44abb15e98d9218b229e
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07098332B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート