5-Bromopyrimidine → HCID 63894507, compound

Participants

Reaction Conditions

Reaction Steps

To an oven-dried flask was added anhydrous THF (40 mL) and 5-bromopyrimidine (6.36 g, 40 mmol). 2M isopropylmagnesium chloride in THF (22 mL) was then added dropwise over several minutes at 0° C. The mixture was stirred at 0° C. for 30 minutes, and then 5-bromo-2-fluorobenzaldehyde (2.4 mL, 20 mmol) was added. After warming to room temperature, the reaction was quenched with saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc, dried over MgSO4, and purified by column chromatography (gradient 0 to 60% EtOAc in hexanes) to afford the product. 1H NMR (400 MHz, CDCl3) δ 9.10 (s, 1H), 8.74 (s, 2H), 7.71 (dd, J=6.4, 2.5 Hz, 1H), 7.43 (ddd, J=8.7, 4.6, 2.6 Hz, 1H), 6.95 (dd, J=9.5, 8.9 Hz, 1H), 6.15 (s, 1H).

Provenance & Evidence