Cesium carbonate → 4-(5-(Difluoromethoxy)-2-fluoropyridin-3-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-fluoropyridin-3-ol (0.050 g, 0.108 mmol) in DMF (3 mL) was treated with sodium 2-chloro-2,2-difluoroacetate (Aldrich) (0.033 g, 0.217 mmol) and cesium carbonate (Aldrich) (0.053 g, 0.163 mmol). The reaction mixture was heated at 100° C. under N2 for 2 h. The reaction mixture was cooled to rt and partitioned between EtOAc and water. The organic layer was washed with sat. NaHCO3, water, brine, dried over MgSO4 and concentrated. The crude product was purified by column chromatography (12 g, 10% to 20% EtOAc in hexanes) to give the product as a white solid (0.030 g). m/z (ESI, +ve ion) 512.0 (M+H)+. 1H NMR (300 MHz, CDCl3) δ 8.39 (d, J=7.45 Hz, 1H); 8.18 (br. s., 1H); 7.23 (d, J=7.89 Hz, 4H); 6.87 (t, J=7.60Hz, 4H); 6.23-6.83 (m, 1H); 4.82 (d, J=8.04 Hz, 4H); 3.81 (d, J=4.82 Hz, 6H); 2.55 (s, 3H).

Provenance & Evidence