Boron tribromide → tert-Butyl 5-amino-2-methylthio-4-(3-hydroxyphenyl)-quinazoline-6-carboxamide

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Reaction Steps

A solution of tert-butyl 5-amino-2-methylthio-4-(3-methoxyphenyl)-quinazoline-6-carboxamide (example 25f, 1.5 g) in dry CH2Cl2 was cooled to 0° C. A solution of BBr3 (1.1 ml) in CH2Cl2 (25 ml) was added dropwise and after the addition was complete, the mixture was stirred for 3 h at room temperature. The mixture was diluted with CH2Cl2 and a saturated aqueous NaHCO3 solution (200 ml) was carefully added. The mixture was vigorously stirred for 1.5 h until all solids dissolved. The aqueous layer was extracted twice with CH2Cl2. The first organic layer was washed with sat. aq. NaHCO3 and brine. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The title compound was purified by chromatography on silica gel with hept/EtOAc=1/0 to 1/1 (v/v) as eluent.

Provenance & Evidence