5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → HCID 58102779, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.30 g (0.75 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole, 0.21 g (0.95 mmol) of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine, and 0.057 g (0.08 mmol) of PdCl2(dppf) in a mixture of 1,4-dioxane (30 mL) and 2M Na2CO3 solution (6 mL) was heated at 100° C. for 5 hrs under nitrogen. After cooling, the mixture was concentrated, diluted with water, and extracted with EtOAc (×4). The organic layer was washed with brine, dried (Na2SO4), and concentrated. Chromatography on silica, eluting first with CH2Cl2-EtOAc (3:1) and then with CH2Cl2-EtOAc (1:3), gave an off-white powder, which was recrystallized from CH2Cl2/EtOH to give 0.144 g (43% yield) of 5-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-pyridinamine: mp 259-261° C.; 1H NMR (DMSO-d6) δ9.04 (d, J=2.2 Hz, 1H), 8.32 (dd, J=8.8, 2.4 Hz, 1H), 8.04 (d, J=8.3 Hz, 1H), 7.79 (t, JHF=52.8 Hz, 1H), 7.47 (t, J=8.2 Hz, 1H), 6.99 (d, J=7.9 Hz, 1H), 6.85 (s, 2H), 6.57 (d, J=8.8 Hz, 1H), 4.04-4.00 (m, 5H), 3.89 (br s, 2H), 3.76 (s, 4H); Anal. Calcd. for C21H20F2N8O20.49H2O: C, 54.45; H, 4.6; N, 24.2. Found: C, 54.8; H, 4.2; N, 24.2%.

Provenance & Evidence