反応 #11885
ord-6595dcbcaa4e4ea4ba99ea2f8bf33099
反応方程式
反応物
試薬
反応条件
後処理
- 1workup.STIRRINGthe reaction mixture was stirred at the same temperature for 1 hour
- 2温度to warm up to −30° C.
- 3workup.STIRRINGstirred for 10 minutes
- 4温度After cooling the reaction mixture
- 5洗浄successively washed with saturated aqueous ammonium chloride solution (50 mL), water (30 mL) and brine (30 mL)
- 6乾燥dried over anhydrous sodium sulfate
- 7ろ過filtered
- 8濃縮concentrated in vacuo
- 9その他The residue was then purified by flash column chromatography
実験手順
To a solution of N-isopropylcyclohexylamine (720 mg, 5.0 mmol) (Aldrich) in dry tetrahydrofuran (10 mL) was added n-butyllithium (2.5 M in hexanes, 2.0 mL, 5.0 mmol) (Aldrich) at −78° C. under argon. After 30 minutes, a solution of 3,4-dimethoxyphenylacetic acid ethyl ester (1.12 g, 5.0 mmol) (Lancaster) in tetrahydrofuran (3 mL) was added by injection via a syringe and the reaction mixture was stirred at −78° C. for another 30 minutes. To the reaction mixture was added a solution of 2,4-dichloro-5-iodomethyl-pyrimidine (722.5 mg, 2.5 mmol) (from Example 1c supra) in tetrahydrofuran (3 mL) at −78° C. and the reaction mixture was stirred at the same temperature for 1 hour then slowly allowed to warm up to −30° C. and stirred for 10 minutes. After cooling the reaction mixture was diluted with ethyl acetate (100 mL) and successively washed with saturated aqueous ammonium chloride solution (50 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 3-(2,4-dichloro-pyrimidin-5-yl)-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester. (Yield 440 mg, 46.0%).