Boron tribromide → HCID 58338024, compound

Participants

Reaction Conditions

Reaction Steps

[2-(2-Fluoro-4-methoxy-phenyl)-ethyl]-thiazolo[5,4-d]pyrimidin-7-ylamine (204 mg, 0.67 mmol) was dissolved in CH2Cl2 (3.4 mL) in a 25 mL round bottom flask equipped with a magnetic stir bar, a septum and a dry nitrogen line. After cooling to 0° C., the solution was treated with 1.0 M boron tribromide (BBr3) solution in CH2Cl2 (3.4 mL), and the reaction mixture became brown. After stirring 3 h at 0° C., the mixture was treated with satd aq sodium bicarbonate (NaHCO3; 10 mL) and stirred at 0° C. for another hour. The precipitate was collected by suction filtration, washed with cold H2O (2×5 mL), and air dried on the filter to provide 3-fluoro-4-[2-(thiazolo[5,4-d]pyrimidin-7-ylamino)-ethyl]phenol (Compound 58; 127 mg) as a beige powder: mp 193° C.; 1H NMR (DMSO-d6) δ 9.64 (br s, 1H), 9.24 (s, 1H), 8.42 (br m, 2H), 7.07 (t, J=8.8 Hz, 1H), 6.53-6.49 (m, 2H), 3.71-3.66 (m, 2H), 2.85 (t, J=7.3 Hz, 2H); ESIMS: m/z 291.2 ([M+H]+).

Provenance & Evidence