反应 #1702140

反应方程式

Water

EtOAc

{3-[(5-chloro-4-{[(1S)-1-(3-methoxyphenyl)ethyl]amino}pyrimidin-2-yl)amino]phenyl}methanol

boron tribromide

water

→

desired product

收率 75.0%

3-{(1S)-1-[(2-{[3-(Bromomethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}phenol

收率 75.0%

溶剂

methylene chloride

methylene chloride

反应条件

后处理

1. 1
   workup.ADDITIONwas added
2. 2
   温度to warm up to rt
3. 3
   萃取The aqueous layer was extracted with EtOAc twice
4. 4
   干燥The combined organic layers were dried over Na2SO4
5. 5
   过滤filtered
6. 6
   浓缩concentrated (
7. 7
   其他then triturated with cold EtOAc)

实验过程

To a solution of {3-[(5-chloro-4-{[(1S)-1-(3-methoxyphenyl)ethyl]amino}pyrimidin-2-yl)amino]phenyl}methanol (0.30 g, 0.78 mmol) in methylene chloride (5.0 mL) was added slowly a solution of boron tribromide in methylene chloride (3.9 mL, 3.9 mmol, 1.0 M) at 0° C. The mixture was allowed to warm up to rt and stirred overnight. The resultant mixture was cooled in a dry ice bath when water was added. The mixture was allowed to warm up to rt. Water and EtOAc were added. The aqueous layer was extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, filtered, and concentrated (then triturated with cold EtOAc) to give the desired product as a white powder (0.255 g, 75%). LCMS for C19H19BrClN4O (M+H)+: m/z=433.0, 435.0.

来源