Ethyl Acetate → 2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2300059Notes

Reaction equation

HRID 2300059 reaction equation
CS([C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[CH:12][C:11](=[O:14])[NH:10][C:8]=2[N:9]=1)=O.CS(C1N=C[C:22]2[CH:28]=[CH:27][C:26](=O)[NH:25][C:23]=2N=1)(=O)=O.[C:30](OCC)(=O)C>NC1C=CC=CC=1>[C:23]1([NH:25][C:4]2[N:5]=[CH:6][C:7]3[CH:13]=[CH:12][C:11](=[O:14])[NH:10][C:8]=3[N:9]=2)[CH:22]=[CH:28][CH:27]=[CH:26][CH:30]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 106084702-(Methylsulfinyl)pyrido[2,3-d]pyrimidin-7(1H)-oneHCID 183749342-(Methylsulfonyl)pyrido[2,3-d]pyrimidin-7(1H)-one

Product 1

HCID 105140732-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 6115AnilineSolvent

Procedure

A suspension of 204 mg of the mixture of 2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one and 2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one in 1 mL of aniline was heated at reflux for 10 minutes resulting in a dark brown solution. Upon cooling to room temperature, a solid formed. Ethyl acetate was added, and the solid was collected by filtration, washed with ethyl acetate, then suspended in methanol and filtered, and washed with additional methanol to provide 175 mg of 2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one, mp>350° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 minutes
  3. customresulting in a dark brown solution
  4. customa solid formed
  5. filtrationthe solid was collected by filtration
  6. washwashed with ethyl acetate
  7. filtrationfiltered
  8. washwashed with additional methanol

Sources & evidence

ORD record
ord-046426131380437b96579baa59856a8a
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

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