반응 #1702124

반응 방정식

NaHCO3

DCM

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

methylene chloride

boron tribromide

methylene chloride

→

desired product

수율 30.0%

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

수율 30.0%

용매

dry ice

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   온도to warm up to rt
3. 3
   추출The aqueous layer was extracted with DCM twice
4. 4
   기타dried
5. 5
   여과filtered
6. 6
   농축concentrated under vacuum
7. 7
   기타The crude product was purified by silica gel column chromatography

실험 절차

Into a 1-neck round-bottom flask were added {3-[(5-chloro-4-{[(1R)-1-(3-methoxyphenyl)ethyl]amino}pyrimidin-2-yl)amino]phenyl}methanol (0.26 g, 0.68 mmol) and methylene chloride (5 mL). To the 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 dry ice 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. The crude product was purified by silica gel column chromatography to give the desired product (40 mg, 30%). LCMS for C19H19BrClN4O (M+H)+: m/z=432.9, 434.9.

출처