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

HRID 11791Notes

Reaction equation

HRID 11791 reaction equation
C([O:3][C:4](=O)[CH:5]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=1)[CH2:6][C:7]1[C:8]([NH:20]C2C=CC=CC=2)=[N:9][C:10]([NH:13]C2C=CC=CC=2)=[N:11][CH:12]=1)C.S(=O)(=O)(O)O.[C:43](O)(=O)[CH3:44]>C(OCC)(=O)C>[CH3:36][O:35][C:29]1[CH:28]=[C:27]([CH:5]2[C:4](=[O:3])[N:20]([C:44]3[CH:43]=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:8]3[N:9]=[C:10]([NH:13][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:11]=[CH:12][C:7]=3[CH2:6]2)[CH:32]=[CH:31][C:30]=1[O:33][CH3:34]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 210443063-(2,4-Diphenylamino-pyrimidin-5-yl)-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester

Product 1

HCID 100268676-(3,4-dimethoxy-phenyl)-8-phenyl-2-phenylamino-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester (470 mg, 0.94 mmol) (from Example 11b supra) in glacial acetic acid (3 mL) was added concentrated sulfuric acid (0.1 mL) in one portion. The reaction mixture was heated at 80° C. overnight. After cooling, 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 which was crystallized from ethyl acetate-hexanes to give 6-(3,4-dimethoxy-phenyl)-8-phenyl-2-phenylamino-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one as a light brown solid. (Yield 335 mg, 78.8%).

Workup

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

Sources & evidence

ORD record
ord-f879e793117f44abb15e98d9218b229e
Source dataset
uspto-grants-2006_08
Patent number
US07098332B2

Reaction notes

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