Boron tribromide → Isobutyl 1-(2-(2-hydroxyphenyl)thieno[3,2-d]pyrimidin-4-yl)piperidin-4-ylcarbamate

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Reaction Steps

A solution of isobutyl 1-(2-(2-methoxyphenyl)thieno[3,2-d]pyrimidin-4-yl)piperidin-4-ylcarbamate (0.13 g, 0.30 mmol) in CH2Cl2 (2 mL) was cooled to −50° C., and a solution of BBr3 in CH2Cl2 (1 M, 1.8 mL, 1.8 mmol) was slowly added. The reaction was allowed to gradually warm to room temperature over 3 h, and saturated aqueous NaHCO3 was slowly added. The organic layer was separated, washed with water, dried over Na2SO4, and concentrated under vacuum. The residue was purified by preparative reverse phase HPLC using 10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) to give isobutyl 1-(2-(2-hydroxyphenyl)thieno[3,2-d]pyrimidin-4-yl)piperidin-4-ylcarbamate. LC/MS: m/z 427.3 (M+H)+ at 3.08 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Provenance & Evidence