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

HRID 11779

Reaktionsgleichung

Reaktionsgleichung von HRID 11779
C[O:2][C:3](=O)[CH:4]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][CH3:33])[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:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH:4]1[C:3](=[O:2])[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7]2[N:8]=[C:9]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[CH:11][C:6]=2[CH2:5]1

Komponenten

5

Edukt 2

HCID 1118Sulfuric AcidHCID 210443173-(2,4-Diphenylamino-pyrimidin-5-yl)-2-(2-methoxy-phenyl) propionic acid methyl ester

Produkt 1

HCID 100937046-(2-methoxy-phenyl)-8-phenyl-2-phenylamino-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-(2-dimethoxy-phenyl propionic acid methyl ester (181.8 mg, 0.40 mmol) (from Example 7b supra) was added 5% concentrated sulfuric acid in glacial acetic acid (3 mL) in one portion. The reaction mixture was heated at 110° C. for 3 hours. After cooling, the reaction mixture was diluted with ethyl acetate (100 mL) and quenched with 2 N aqueous sodium hydroxide solution. The organic layer was separated and successively washed with water (30 mL) and brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give the crude product. The crude product was crystallized from ethyl acetate-hexanes to give 6-(2-methoxy-phenyl)-8-phenyl-2-phenylamino-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one as an off-white solid. (Yield 119.4 mg, 67.2%).

Aufarbeitung

  1. temperatureAfter cooling
  2. customquenched with 2 N aqueous sodium hydroxide solution
  3. customThe organic layer was separated
  4. washsuccessively washed with water (30 mL) and brine (30 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude product
  9. customThe crude product was crystallized from ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8312e661429447d69f797ea2a7092eb8
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098332B2

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