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

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Reaction Steps

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.

Provenance & Evidence