Potassium Carbonate → HCID 49869215, compound

Participants

Reaction Steps

Similarly to Example 56, a mixture of 1-[4-chloro-6-(4-morpholinyl)-2-pyrimidinyl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole (148 mg, 0.374 mmol), 2-methoxy-5-pyrimidinylboronic acid (211 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 were removed under vacuum. Chromatography on silica, eluting with CH2Cl2/MeOH (100:0 to 98:2), followed by recrystallization from CH2Cl2/MeOH/i-Pr2O gave 2-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-2′-methoxy-4,5′-bipyrimidine (61 mg, 35%): mp 238-241° C.; 1H NMR (CDCl3) δ 9.18 (s, 2H), 7.91 (d, J=8.1 Hz, 1H), 7.49 (t, JHF=53.6 Hz, 1H), 7.37 (t, J=8.2 Hz, 1H), 6.83 (d, J=7.9 Hz, 1H), 6.77 (s, 1H), 4.13 (s, 3H), 4.07 (s, 3H), 3.88 (dd, J=5.6, 3.7 Hz, 4H), 3.82 (m, 4H); Anal. Calcd. for C22H21F2N7O3: C, 56.3; H, 4.5; N, 20.9. Found: C, 56.1; H, 4.3; N, 20.6%.

Provenance & Evidence