تفاعل #1702124

معادلة التفاعل

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

المردود 30.0%

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

المردود 30.0%

المذيبات

dry ice

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   درجة الحرارةto warm up to rt
3. 3
   استخلاصThe aqueous layer was extracted with DCM twice
4. 4
   أخرىdried
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated under vacuum
7. 7
   أخرىThe crude product was purified by silica gel column chromatography

الإجراء التجريبي

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.

المصدر