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

Reaktionsgleichung

Reaktionsgleichung von HRID 11794
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

Komponenten

5

Edukt 2

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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0cc76f6a46d14480921745d16f372339
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098332B2

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