反応 #1702136

反応方程式

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

boron tribromide

water

→

desired product

収率 75.0%

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

収率 75.0%

溶媒

methylene chloride

methylene chloride

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度to warm up to rt
3. 3
   その他After methylene chloride layer was separated
4. 4
   workup.ADDITIONwater and EtOAc were added
5. 5
   抽出The aqueous layer was extracted with EtOAc twice
6. 6
   乾燥The combined organic layers were dried over Na2SO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated (
9. 9
   その他then triturated with cold EtOAc)

実験手順

To a solution of {3-[(5-chloro-4-{[3-(3-methoxyphenyl)propyl]amino}pyrimidin-2-yl)amino]phenyl}methanol (0.30 g, 0.75 mmol) in methylene chloride (4.8 mL) was added slowly a solution of boron tribromide in methylene chloride (3.8 mL, 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. After methylene chloride layer was separated, 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 an off-white powder (252 mg, 75%). LCMS for C20H21BrClN4O (M+H)+: m/z=447.0, 449.0. 1H NMR (400 MHz, CD3OD): δ 7.92 (s, 1H), 7.63 (s, 1H), 7.39 (s, 1H), 7.38 (m, 2H), 7.03 (t, J=7.2 Hz, 1H), 6.61 (m, 2H), 6.58 (s, 1H), 4.56 (s, 2H), 3.60 (t, J=7.6 Hz, 2H), 2.58 (t, J=7.6 Hz, 2H), 1.96 (m, 2H).

出典