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

HRID 11794

反応式

HRID 11794 の反応式
CO[C:3](=[O:36])[CH:4]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)[CH2:5][C:6]1[C:7]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:8][C:9]([NH:12][C:13]2[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[N:10][CH:11]=1.S(=O)(=O)(O)O>C(O)(=O)C.C(OCC)(=O)C>[CH3:35][O:34][C:31]1[CH:32]=[CH:33][C:28]([CH:4]2[C:3](=[O:36])[N:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:7]3[N:8]=[C:9]([NH:12][C:13]4[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=4)[N:10]=[CH:11][C:6]=3[CH2:5]2)=[CH:29][CH:30]=1

参加物

5

反応物 2

HCID 1118Sulfuric AcidHCID 210443183-[2-(6-Methoxy-pyridin-3-ylamino)-4-phenylamino-pyrimidin-5-yl]-2-(4-methoxy-phenyl)-propionic acid methyl ester

生成物 1

HCID 100269256-(4-methoxy-phenyl)-2-(6-methoxy-pyridin-3-ylamino)-8-phenyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidine-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 a solution of 3-[2-(6-methoxy-pyridin-3-ylamino)-4-phenylamino-pyrimidin-5-yl]-2-(4-methoxy-phenyl)-propionic acid methyl ester (45.0 mg, 0.09 mmol) (from Example 12c supra) in glacial acetic acid (1 mL) was added concentrated sulfuric acid (0.1 mL) in one portion. After heating at 80° C. for 3 hours, 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. The crude product was purified by preparative thin layer chromatography to give 6-(4-methoxy-phenyl)-2-(6-methoxy-pyridin-3-ylamino)-8-phenyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidine-7-one as brown powder. (Yield 5.2 mg, 12.4%).

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 product
  8. customThe crude product was purified by preparative thin layer chromatography

出典と根拠

ORDレコード
ord-0cc76f6a46d14480921745d16f372339
出典データセット
uspto-grants-2006_08
特許番号
US07098332B2

関連ノート

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