3-Fluoro-2-methoxyaniline → 8-ethyl 2-(3-fluoro-2-methoxyphenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2300080Notes

Reaction equation

HRID 2300080 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[C:19]([O:25][CH3:26])=[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])[C:19]=3[O:25][CH3:26])[N:11]=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]1=[O:16])[CH3:2]

Participants

3

Reactant 2

HCID 5811093-Fluoro-2-methoxyanilineHCID 10752351Pyrido[2,3-d]pyrimidin-7(8H)-one, 8-ethyl-2-(methylsulfinyl)-

Product 1

HCID 183748748-ethyl 2-(3-fluoro-2-methoxyphenylamino)-8H-pyrido[2,3-d]pyrimidin-7-oneYield 16%

Conditions

Temperature
175 °C

Procedure

A mixture of 8-ethyl-2-methylsulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (133 mg, 0.56 mmol) and 500 μL of 3-fluoro-2-methoxyaniline was heated at 175° C. for 20 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 ethyl acetate and hexane provided 28 mg (16%) of 8-ethyl 2-(3-fluoro-2-methoxyphenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one, mp 92-93° 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 ethyl acetate and hexane

Sources & evidence

ORD record
ord-d8df43f1f890460ab3787ae6299d2458
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

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