Ethyl Acetate → 2-(4,6-Dimethoxypyrimidine-2-ylcarbonyl)aniline

HRID 2112243Notes

Reaction equation

HRID 2112243 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13]C=2C)[N:4]=1.C(OCC)(=[O:23])C.O=[O+][O-]>O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]([C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH2:13])=[O:23])[N:4]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24823OzoneHCID 129793683-(4,6-Dimethoxypyrimidine-2-yl)-2-methylindole2×

Product 1

HCID 178567502-(4,6-Dimethoxypyrimidine-2-ylcarbonyl)anilineYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a reactor were placed 0.60 g (22 m moles) of 3-(4,6-dimethoxypyrimidine-2-yl)-2-methylindole and 20 ml of ethyl acetate. Thereinto was blown ozone at 0° C. to 10° C. for 4 hours. Thin-layer chromatography was conducted to confirm the disappearance of 3-(4,6-dimethoxypyrimidine-2-yl)-2-methylindole and complete a reaction. Then, the reaction mixture was heated to room temperature and concentrated. To the concentrate were added 20 ml of methanol and 5 ml of 6 N hydrochloric acid, and refluxing was made for 1 hour with heating. After the completion of the reaction, the reaction mixture was cooled to room temperature. 100 ml of water was added. The mixture was made alkaline with an aqueous sodium hydroxide solution, and extraction was made with ethyl acetate. The organic layer was concentrated. The concentrate was subjected to column chromatography separation to obtain 0.26 g (10 m moles) of 2-(4,6-dimethoxypyrimidine-2-ylcarbonyl)aniline. Yield: 46%

Workup

  1. customIn a reactor were placed
  2. customat 0° C. to 10° C.
  3. customfor 4 hours
  4. customa reaction
  5. concentrationconcentrated
  6. additionTo the concentrate were added 20 ml of methanol and 5 ml of 6 N hydrochloric acid
  7. temperaturerefluxing
  8. temperaturewith heating
  9. customAfter the completion of the reaction
  10. temperaturethe reaction mixture was cooled to room temperature
  11. extractionwith an aqueous sodium hydroxide solution, and extraction
  12. concentrationThe organic layer was concentrated
  13. customThe concentrate was subjected to column chromatography separation

Sources & evidence

ORD record
ord-dbbbc4266a4a48949571f1309f88d918
Source dataset
uspto-grants-2009_04
Patent number
US07521555B2

Reaction notes

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