Reaction #1702126

Reaction equation

NaHCO3

boron tribromide

5-chloro-N(4)-(3-methoxybenzyl)-N(2)-(3-methoxyphenyl)pyrimidine-2,4-diamine

→

desired product

Yield 58.3%

3-({5-Chloro-4-[(3-hydroxybenzyl)amino]pyrimidin-2-yl}amino)phenol

Yield 58.3%

Solvents

DCM

methylene chloride

methylene chloride

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 5-chloro-N(4)-(3-methoxybenzyl)-N(2)-(3-methoxyphenyl)pyrimidine-2,4-diamine (90 mg, 0.2 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 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 (40 mg, 50%). LCMS for C17H16ClN4O2 (M+H)+: m/z=343.0.

Source