Potassium Carbonate → HCID 58102805, compound

Participants

Reaction Steps

Similarly to Example 55, a mixture of 1-[4-chloro-6-(4-morpholinyl)-2-pyrimidinyl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole (106 mg, 0.268 mmol), pyrimidine-5-boronic acid (188 mg, 1.52 mmol), PdCl2(dppf) (40 mg, 0.05 mmol) and aq. K2CO3 (2M, 4 mL) in 1,4-dioxane (20 mL) was refluxed under nitrogen for 24 hrs. After cooling to room temperature, the mixture was diluted with H2O, and extracted with CH2Cl2 (4×). The combined organic extracts were dried (Na2SO4), and the solvents removed under vacuum. Chromatography on silica, eluting with CH2Cl2/MeOH (100:0 to 97:3), followed by recrystallization from CH2Cl2/MeOH/hexanes gave 2-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-4,5′-bipyrimidine (89 mg, 75%): mp 222-224° C.; 1H NMR (CDCl3) δ 9.38 (s, 2H), 9.36 (s, 1H), 7.92 (dd, J=8.4, 0.6 Hz, 1H), 7.49 (t, J=53.6 Hz, 1H), 7.38 (t, J=8.2 Hz, 1H), 6.86 (s, 1H), 6.84 (d, J=7.7 Hz, 1H), 4.07 (s, 3H), 3.89 (m, 4H), 3.85 (m, 4H); Anal. Calcd. for C21H19F2N7O20.25 MeOH: C, 57.0; H, 4.5; N, 21.9. Found: C, 56.95; H, 4.45; N, 22.0%.

Provenance & Evidence