Hexane → 5-Chloro-3-(2,4-dimethoxypyrimidin-5-yl)-3-hydroxy-1,3-dihydroindol-2-one

温度

-78 °C

A 1.6 M solution of n-butyllithium in hexane (10 ml, 16 mmol) was added dropwise to a solution of 5-bromo-2,4-dimethoxypyrimidine (3.29 g, 15 mmol) in THF (50 ml) at −78° C. After stirring at −78° C. for 0.5 h, a suspension of 5-chloroisatin (1.27 g, 7.0 mmol) in THF (50 ml) was added dropwise. The reaction mixture was allowed to warm to room temperature and then saturated ammonium chloride solution was added. The mixture was extracted three times with ethyl acetate, and the combined organic layers were washed with saturated brine. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by chromatography (silica gel, 50% ethyl acetate in dichloromethane) resulted in 0.97 g of the intermediate.

1. additionwas added dropwise
2. temperatureto warm to room temperature
3. extractionThe mixture was extracted three times with ethyl acetate
4. washthe combined organic layers were washed with saturated brine
5. dry with materialThe organic phase was dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customPurification by chromatography (silica gel, 50% ethyl acetate in dichloromethane)

ORDレコード

ord-7adaf7ffb7214d29a178fe10515f228e

出典データセット

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07902379B2