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

HRID 11783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 11783
C[O:2][C:3](=O)[CH:4]([C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[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>[F:39][C:36]([F:38])([F:37])[C:28]1[CH:27]=[C:26]([CH:4]2[C:3](=[O:2])[N:19]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:7]3[N:8]=[C:9]([NH:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:10]=[CH:11][C:6]=3[CH2:5]2)[CH:31]=[C:30]([C:32]([F:34])([F:35])[F:33])[CH:29]=1

Komponenten

5

Edukt 2

HCID 1118Sulfuric AcidHCID 210443263-(2,4-Diphenylamino-pyrimidin-5-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-propionic acid methyl ester

Produkt 1

HCID 104595846-(3,5-bis-trifluoromethyl-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
120 °C

Versuchsvorschrift

To a solution of 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-propionic acid methyl ester (0.20 g, 0.36 mmol) (from Example 8c supra) was added 5% concentrated sulfuric acid in glacial acetic acid (3 mL) in one portion. The reaction mixture was heated at 120° C. for 3 hours. The reaction mixture was then 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 which was crystallized from ethyl acetate-hexanes to give 6-(3,5-bis-trifluoromethyl-phenyl)-8-phenyl-2-phenylamino-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one as an off-white solid. (Yield 130.3 mg, 70.5%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-fd307c631251414fb63b7d58f5f8cce4
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098332B2

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