Aniline → 3-(2,4-Diphenylamino-pyrimidin-5-yl)-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester

HRID 11790Notes

Reaction equation

HRID 11790 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH:5]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1)[CH2:6][C:7]1[C:8](Cl)=[N:9][C:10](Cl)=[N:11][CH:12]=1)[CH3:2].[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:1]([O:3][C:4](=[O:25])[CH:5]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1)[CH2:6][C:7]1[C:8]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:9][C:10]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:11][CH:12]=1)[CH3:2]

Participants

3

Reactant 2

HCID 6115AnilineHCID 21044302HCID 21044302, compound

Product 1

HCID 210443063-(2,4-Diphenylamino-pyrimidin-5-yl)-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester

Conditions

Temperature
110 °C

Procedure

A mixture of 3-(2,4-dichloro-pyrimidin-5-yl)-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester (440 mg, 1.1 mmol) (from Example 11a supra) and aniline (2.0 mL) (Aldrich) was heated at 110° C. for 2 hours. The reaction mixture was washed with hexanes (50 mL×3) and the supernatant was decanted off after each time. The residue was then dissolved in ethyl acetate (100 mL) and successively washed with saturated aqueous ammonium chloride solution (30 mL), water (30 mL) and brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was then purified by flash column chromatography to give the crude 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester as an off-white solid. (Yield 470 mg, 86%).

Workup

  1. washThe reaction mixture was washed with hexanes (50 mL×3)
  2. customthe supernatant was decanted off after each time
  3. dissolutionThe residue was then dissolved in ethyl acetate (100 mL)
  4. washsuccessively washed with saturated aqueous ammonium chloride solution (30 mL), water (30 mL) and brine (30 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified by flash column chromatography

Sources & evidence

ORD record
ord-7e15299e24944a1ea8f3d98132393c75
Source dataset
uspto-grants-2006_08
Patent number
US07098332B2

Reaction notes

Loading…