Methyl 2,4-dichloropyrimidine-6-carboxylate → HCID 86633637, compound

Participants

Reaction Conditions

Reaction Steps

Pd(dppf)Cl2 (0.214 g, 0.02 mmol) was added to a mixture of methyl 2,4-dichloropyrimidine-6-carboxylate (2.07 g, 10 mmol) and 4-(trifluoromethyl)phenyl-boronic acid (1.90 g, 10 mmol) in DME (100 mL) and sat. aq. NaHCO3 (20 mL), and the mixture was stirred in an atmosphere of argon at 80° C. for 3 h. The reaction mixture was cooled to 20° C. and added to ice water (100 mL). The mixture was extracted with ethyl acetate (2×100 mL) and the organic phase was extracted with saturated sodium carbonate solution (50 mL). The combined aqueous layers were acidified by the addition of 25% HCl (100 mL) and subsequently extracted with ethyl acetate (2×100 mL). The organic phase was washed with brine, dried over sodium sulfate, and the solvents were removed under reduced pressure. The residual solid was recrystallized from ethyl acetate/heptane to give the title compound (1.82 g, 60%) as light red solid. MS ISN (m/e): 301.2 [(M−H)−]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.51 (s, 1H), 8.33 and 7.84 (2 d, 2×2H).

Provenance & Evidence