Aniline → 8-Ethyl-6-methyl-2-(phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 2300073Notes

Reaction equation

HRID 2300073 reaction equation
[CH2:1]([N:3]1[C:8]2[N:9]=[C:10](S(C)=O)[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]([CH3:16])[C:4]1=[O:17])[CH3:2].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:1]([N:3]1[C:8]2[N:9]=[C:10]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]([CH3:16])[C:4]1=[O:17])[CH3:2]

Participants

3

Reactant 2

HCID 6115AnilineHCID 9878213HCID 9878213, compound

Product 1

HCID 99217778-Ethyl-6-methyl-2-(phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 15%

Conditions

Temperature
175 °C

Procedure

A mixture of 8-ethyl-6-methyl-2-methylsulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (123 mg, 0.49 mmol) and 1 mL of aniline was heated at 175° C. for 20 minutes. The reaction was cooled to room temperature and partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated. Hexane was added to the residue, and the resultant solid was collected by filtration and purified by flash chromatography eluting with ethyl acetate to provide 21 mg (15%) of 8-ethyl-6-methyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one, mp 178-180° C.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. custompartitioned between ethyl acetate and saturated sodium bicarbonate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionHexane was added to the residue
  8. filtrationthe resultant solid was collected by filtration
  9. custompurified by flash chromatography
  10. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-9117d7c46e7741e1a4957c4dc1dd70a0
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

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