Dimethylformamide → HCID 59852844, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-4-(2-fluoro-4-nitrophenoxy)pyrimidine (0.66 g, 2.44 mmol), 4-methoxybenzylamine (0.34 g, 3.45 mmol), K2CO3 (0.37 g, 2.66 mmol), and DMF (15 mL) was heated at 100° C. for 1 h. The mixture was cooled, diluted with H2O (100 mL) and extracted with EtOAc (100 mL). The organic phase was washed twice each with saturated NaHCO3 solution and brine. The organics were dried (MgSO4) and concentrated to give the crude product. Flash chromatography on SiO2 using 1-3% MeOH in CH2Cl2 as the eluent gave the title compound (275 mg, 29%) as a pale yellow solid. 1H NMR (DMSO-d6) δ 8.40-8.21 (m, 2H), 8.16 (dd, 1H, J=8.8, 1.7 Hz), 7.98 (br s, 0.5H), 7.73-7.55 (m, 1.5 H), 7.16 (br s, 1H), 6.85-6.71 (m, 3H), 6.37 (s, 1H), 4.43 (br s, 1H), 3.95 (br s, 1H), 3.69 (s, 3H).

Provenance & Evidence