5-Amino-2-chloropyridine → HCID 58102798, compound

Participants

Reaction Steps

To 0.246 g (1.92 mmol) of 5-amino-2-chloropyridine in THF (4 mL) was added 0.85 mL of n-butyllithium (2.5 M solution in hexanes), and the mixture was stirred for 10 min. A solution of 0.260 g (0.66 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole (Example 2) in THF (5 mL) was added. The resulting mixture was stirred at room temperature for 1 hr. After neutralization with acetic acid, the mixture was diluted with water and extracted with EtOAc. The organic layer was washed successively with water and aqueous NH3, and dried. Removal of the solvent and chromatography of the residue on alumina eluting first with hexanes/EtOAc (1:1) and then with CH2Cl2-EtOAc (1:5) gave a brown powder. Recrystallization from ethanol/CH2Cl2 gave 0.016 g (5% yield) of N-(6-chloro-3-pyridinyl)-4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-amine: mp 260-262° C.; 1H NMR (CDCl3) δ8.69 (s, 1H), 7.95-7.90 (m, 2H), 7.48 (t, J=53.5 Hz, 1H), 7.37-7.33 (m, 2H), 7.11 (s, 1H), 6.83 (d, J=8.0 Hz, 1H), 4.05 (s, 3H), 3.94-3.87 (m, 4H), 3.81 (m, 4H); Anal. Calcd. for C21H19ClF2N8O2: C, 51.6; H, 3.9; N, 22.9; Cl, 7.25. Found: C, 52.1; H, 3.9; N, 22.5; Cl, 7.1%.

Provenance & Evidence