Reaction #1702121

Reaction equation

NaHCO3

boron tribromide

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

→

desired product

Yield 74.0%

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

Yield 74.0%

Solvents

DCM

methylene chloride

DCM

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Temperatureto warm up to rt
3. 3
   ExtractionThe aqueous layer was extracted with DCM twice
4. 4
   Otherdried
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under vacuum

Procedure

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.

Source