4-Fluoroaniline → 8-ethyl-2-(4-fluorophenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2300077Notes

Reaction equation

HRID 2300077 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:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1>>[CH2:1]([N:3]1[C:8]2[N:9]=[C:10]([NH:22][C:21]3[CH:23]=[CH:24][C:18]([F:17])=[CH:19][CH:20]=3)[N:11]=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]1=[O:16])[CH3:2]

Participants

3

Reactant 2

HCID 97314-FluoroanilineHCID 10752351Pyrido[2,3-d]pyrimidin-7(8H)-one, 8-ethyl-2-(methylsulfinyl)-

Product 1

HCID 53302068-ethyl-2-(4-fluorophenylamino)-8H-pyrido[2,3-d]pyrimidin-7-oneYield 49%

Conditions

Temperature
175 °C

Procedure

A mixture of 8-ethyl-2-methylsulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (145 mg, 0.61 mmol) and 500 μL of 4-fluoroaniline was heated at 175° C. for 10 minutes. The reaction mixture was cooled to room temperature, and the resultant solid was washed with 1:1 hexane:ethyl acetate. The solid was purified by flash chromatography eluting with ethyl acetate to provide 85 mg (49%) of 8-ethyl-2-(4-fluorophenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one, mp 215-217° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washthe resultant solid was washed with 1:1 hexane
  3. customThe solid was purified by flash chromatography
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-4de9f5af26e04790bab731f73f045581
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

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