Aniline → HCID 5330235, compound

HRID 2300084Notes

Reaction equation

HRID 2300084 reaction equation
CS([C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[CH:12][C:11](=[O:14])[N:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[N:9]=1)=O.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCCCCC>C(OCC)(=O)C>[C:22]1([NH:21][C:4]2[N:5]=[CH:6][C:7]3[CH:13]=[CH:12][C:11](=[O:14])[N:10]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:8]=3[N:9]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8058HexaneHCID 10731849HCID 10731849, compound

Product 1

HCID 5330235HCID 5330235, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of 2-methanesulfinyl-8-phenyl-8H-pyrido[2,3-d]pyrimidin-7-one (197 mg, 0.69 mmol) and 1 mL of aniline was heated at 175° C. for 10 minutes then cooled to room temperature. Hexane and ethyl acetate were added, and the solid was collected by filtration and purified by flash chromatography eluting with ethyl acetate. The fractions containing product were concentrated, and the residue was recrystallized first from hexane and ethyl acetate then from chloroform and ethyl acetate to provide 85 mg (39%) of 2-phenylamino-8-phenyl-8H-pyrido[2,3-d]pyrimidin-7-one, mp 300-302° C.

Workup

  1. temperaturethen cooled to room temperature
  2. filtrationthe solid was collected by filtration
  3. custompurified by flash chromatography
  4. washeluting with ethyl acetate
  5. additionThe fractions containing product
  6. concentrationwere concentrated
  7. customthe residue was recrystallized first from hexane and ethyl acetate

Sources & evidence

ORD record
ord-119f3b5a90434cb8abb13e13475b2816
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

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