반응 #11887

반응 방정식

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

sulfuric acid

acetic acid

→

6-(3,4-dimethoxy-phenyl)-8-phenyl-2-phenylamino-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

용매

ethyl acetate

반응 조건

후처리

1. 1
   온도After cooling
2. 2
   기타quenched with 2 N aqueous sodium hydroxide solution
3. 3
   기타The organic layer was separated
4. 4
   세척successively washed with water (10 mL) and brine (10 mL)
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo
8. 8
   기타to give the crude product which
9. 9
   기타was crystallized from ethyl acetate-hexanes

실험 절차

To a solution of 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester (470 mg, 0.94 mmol) (from Example 11b supra) in glacial acetic acid (3 mL) was added concentrated sulfuric acid (0.1 mL) in one portion. The reaction mixture was heated at 80° C. overnight. After cooling, the reaction mixture was diluted with ethyl acetate (50 mL) and quenched with 2 N aqueous sodium hydroxide solution. The organic layer was separated and successively washed with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give the crude product which was crystallized from ethyl acetate-hexanes to give 6-(3,4-dimethoxy-phenyl)-8-phenyl-2-phenylamino-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one as a light brown solid. (Yield 335 mg, 78.8%).

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