Iodine → 2-(4-(tert-Butyldimethylsilyloxy)benzyl)pyrimidine

Participants

Reaction Steps

Zinc (0.33 g, 4.97 mmol) and iodine (0.008 g, 0.033 mmol) were added to an oven-dried flask (25 mL). The mixture was heated under vacuum with a heat gun for 10 min, cooled to RT, placed under argon atmosphere, suspended in 3 mL DMF (dry, degassed by bubbling nitrogen through it for 10 min), and cooled to 0° C. (4-(Bromomethyl)phenoxy)(tertbutyl)dimethylsilane (1.00 g, 3.31 mmol) was added as a solution in 3 mL DMF, the mixture was stirred at 0° C. for 30 min, then room temperature for 30 min. Next, 2-bromopyrimidine (526 mg, 3.31 mmol), Pd2 dba3 (0.091 mg, 0.099 mmol), and S-Phos (0.163 g, 0.40 mmol) were added. The flask was purged with argon and heated for 1 h at 60° C., cooled to RT, filtered through Celite, and concentrated in vacuo. The resulting solid was purified by flash chromatography to give title compound as a light yellow oil. MS (ESI) m/z: Calculated: 300.2; Observed: 301.5 (M++1).

Provenance & Evidence