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

HRID 11764ノート

反応式

HRID 11764 の反応式
C[O:2][C:3](=O)[CH:4]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[CH2:5][C:6]1[C:7]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:8][C:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][CH:11]=1.S(=O)(=O)(O)O>C(O)(=O)C.C(OCC)(=O)C>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([CH:4]2[C:3](=[O:2])[N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:7]3[N:8]=[C:9]([NH:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:10]=[CH:11][C:6]=3[CH2:5]2)=[CH:27][CH:28]=1

参加物

5

反応物 2

HCID 1118Sulfuric AcidHCID 210443163-(2,4-Diphenylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester

生成物 1

HCID 100708676-(4-methoxy-phenyl)-8-phenyl-2-phenylamino-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To the solution of 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester (227.3 mg, 0.5 mmol) (from Example 1e supra) in glacial acetic acid (15 mL) was added concentrated sulfuric acid (0.2 mL) in one portion. The reaction mixture was heated at 80° C. overnight. The reaction mixture was then 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 products which was crystallized from ethyl acetate-hexanes to give 6-(4-methoxy-phenyl)-8-phenyl-2-phenylamino-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one as brown crystalline solid. (Yield 174.2 mg, 82.4%).

後処理

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

出典と根拠

ORDレコード
ord-72569249a4644535976a717f79b97131
出典データセット
uspto-grants-2006_08
特許番号
US07098332B2

反応ノート

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