Aniline → 3-(2,4-Diphenylamino-pyrimidin-5-yl)-2-pyridin-3-yl-propionic acid ethyl ester
반응식
[CH2:1]([O:3][C:4](=[O:21])[CH:5]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:6][C:7]1[C:8](Cl)=[N:9][C:10](Cl)=[N:11][CH:12]=1)[CH3:2].[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:1]([O:3][C:4](=[O:21])[CH:5]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:6][C:7]1[C:8]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:9][C:10]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:11][CH:12]=1)[CH3:2]참가 물질
반응 조건
- 온도
- 120 °C
실험 절차
A mixture of 3-(2,4-dichloro-pyrimidin-5-yl)-2-pyridin-3-yl-propionic acid ethyl ester (326 mg, 1.0 mmol) (from Example 10a supra) and aniline (2.0 mL) (Aldrich) was heated at 120° C. for 1 hour. 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 crude product was purified by preparative thin layer chromatography to give 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-pyridin-3-yl-propionic acid ethyl ester as a brown solid which was used in the next step without further purification. (Yield 60 mg, 13.7%).
후처리
- washThe reaction mixture was washed with hexanes (50 mL×3)
- customthe supernatant was decanted off after each time
- dissolutionThe residue was then dissolved in ethyl acetate (100 mL)
- washsuccessively washed with saturated aqueous ammonium chloride solution (30 mL), water (30 mL) and brine (30 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was purified by preparative thin layer chromatography
출처 및 근거
- ORD 기록
- ord-574db29389fe441fb2573534e99b8d0c
- 출처 데이터셋
- uspto-grants-2006_08
- 특허 번호
- US07098332B2
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