Nitrogen → 2-Benzyl-4-methoxypyrimidine

Participants

Reaction Steps

A solution of 2-chloro -4-methoxypyrimidine (0.500 g, 3.46 mmol) and PdCl2(PPh3)2 (0.121 g, 0.173 mmol) in THF (10 mL) was sparged with N2. Benzylzinc(II) bromide (8.30 mL, 4.15 mmol; 0.5 M solution in THF) was added and the reaction mixture was stirred at reflux for 1 hour. The reaction mixture was cooled to room temperature and then partitioned between EtOAc and H2O. The phases were separated, and the aqueous phase was re-extracted with EtOAc (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated to yield a crude dark brown oil. The crude product was purified by flash column chromatography, eluting with 20:1 dichloromethane/EtOAc. The desired product (0.676 g, 98%) was obtained as a dark yellow oil. 1H NMR (400 MHz, CDCl3) δ8.34 (d, J=5.9 Hz, 1H), 7.41-7.25 (m, 4H), 7.21 (m, 1H), 6.53 (d, J=5.5 Hz, 1H), 4.16 (s, 2H), 3.95 (s, 3H). LRMS (ESI pos) m/e 201 (M+1).

Provenance & Evidence