Cesium carbonate → 5-Bromo-1-(2-(tert-butyldimethylsilyloxy)ethyl)pyrimidin-2(1H)-one

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Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-pyrimidinone (5.3 g, 30 mmol) in N,N-dimethylformamide (50 mL) was added (2-bromoethoxy)(tert-butyl)dimethylsilane (8.5 mL, 39 mmol) and cesium carbonate (12 g, 36 mmol). The mixture was stirred at 25° C. for 3 days, then poured into aq. NaHCO3 (500 mL) and extracted with 50% EtOAc/hexane (3×200 mL). The combined extracts were washed with H2O (3×200 mL) and brine (200 mL) and then dried (Na2SO4) and concentrated to afford a brown solid. Recrystallization from EtOAc/hexane afforded the title compound as an off-white crystalline solid (6.0 g, 59% yield). MS (ESI, pos. ion.) m/z: 333 (MH+). Calc'd exact mass for C12H21BrN2O2Si: 333. 1H NMR (400 MHz, DMSO-d6) δ ppm −0.08 (s, 6 H), 0.80 (s, 9 H), 3.81 (t, J=5.0 Hz, 2 H), 3.96 (t, J=5.0 Hz, 2 H), 8.40 (d, J=3.3 Hz, 1 H), 8.63 (d, J=3.3 Hz, 1 H).

Provenance & Evidence