反応 #1702121

反応方程式

NaHCO3

boron tribromide

3-[3-({5-chloro-4-[(3-methoxybenzyl)amino]pyrimidin-2-yl}amino)phenyl]propan-1-ol

→

desired product

収率 74.0%

3-{[(2-{[3-(3-Bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]methyl}phenol

収率 74.0%

溶媒

DCM

methylene chloride

DCM

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度to warm up to rt
3. 3
   抽出The aqueous layer was extracted with DCM twice
4. 4
   その他dried
5. 5
   ろ過filtered
6. 6
   濃縮concentrated under vacuum

実験手順

Into a 1-neck round-bottom flask were added 3-[3-({5-chloro-4-[(3-methoxybenzyl)amino]pyrimidin-2-yl}amino)phenyl]propan-1-ol (0.18 g, 0.45 mmol) and DCM (5 mL). To the reaction mixture was added a solution of boron tribromide in methylene chloride (3.0 mL, 3.0 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 NaHCO3 (saturated aqueous solution, 10 mL) was added. The mixture was allowed to warm up to rt and DCM was added. The aqueous layer was extracted with DCM twice. The organic layers were combined, dried, filtered, and concentrated under vacuum to give the desired product as an off-white powder (150 mg, 74%). LCMS for C20H21BrClN4O (M+H)+: m/z=447.0, 449.0.

出典