3-Fluoroaniline → 8-ethyl-2-(3-fluorophenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2300078Notes

Reaction equation

HRID 2300078 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]=[CH:5][C:4]1=[O:16])[CH3:2].[F:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21]>>[CH2:1]([N:3]1[C:8]2[N:9]=[C:10]([NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[C:18]([F:17])[CH:19]=3)[N:11]=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]1=[O:16])[CH3:2]

Participants

3

Reactant 2

HCID 97423-FluoroanilineHCID 10752351Pyrido[2,3-d]pyrimidin-7(8H)-one, 8-ethyl-2-(methylsulfinyl)-

Product 1

HCID 53302078-ethyl-2-(3-fluorophenylamino)-8H-pyrido[2,3-d]pyrimidin-7-oneYield 25%

Conditions

Temperature
175 °C

Procedure

A mixture of 8-ethyl-2-methylsulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (112 mg, 0.47 mmol) and 500 μL of 3-fluoroaniline was heated at 175° C. for 10 minutes. The reaction mixture 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 in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate. Recrystallization from chloroform and hexane provided 33 mg (25%) of 8-ethyl-2-(3-fluorophenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one, mp 210-212° C.

Workup

  1. temperatureThe reaction mixture 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 in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with ethyl acetate
  9. customRecrystallization from chloroform and hexane

Sources & evidence

ORD record
ord-fa353838f7fb494b84ef7e612774cfe6
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

Loading…