Ethanol → 2-Chloro-4-phenylpyrimidine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2,4-dichloropyrimidine (1.47 g, 9.8 mmol), benzene boronic acid (1 g, 8.2 mmol), Na2CO3 (2.61 g, 24.61=01) in a mixture of DME (15 ml), EtOH (2 ml) and water (3 ml) was added Pd(PPh3)4 (190 mg, 0.16 mmol) and the resulting mixture heated in a microwave at 125° C. for 30 min. The reaction was repeated on same scale. The reaction mixtures were combined and diluted with water and extracted with EtOAc (×2). The EtOAc layers were combined and washed with sat. NaCl, dried over MgSO4, filtered and evaporated. The residue was purified by MPLC (Biotage Horizon: FLASH 40+M) eluent: 100% Hexanes (180 ml), gradient rising from 100% Hexanes to 10% EtOAc in Hexanes (900 ml), then 10% EtOAc in Hexanes (500 ml) to give 1.3 g of the title compound (41%) as a white solid. 1H NMR (CDCl3): 7.54 (m, 3H), 7.76 (s, 1H), 8.08 (m, 2H), 9.04 (s, 1H).

Provenance & Evidence