反应详情

温度

120 °C

To a solution of 5-[2-(2-bromo-phenyl)-1-tert-butyl-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine (refer to example 8, step 1) (57 mg, 0.14 mmol) in DMF (5 mL) are added 1H-1,2,3-triazole (0.012 mL, 0.2 mmol), CuO (1 mg, 0.013 mmol), Fe(acac)3 (14 mg, 0.04 mmol) and Cs2CO3 (88 mg, 0.27 mmol) at room temperature. The mixture is heated at 120° C. for 96 hours and then cooled down and filtered. The filtrate is extracted with H2O (10 mL) and EtOAc (3×10 mL). The combined organic layer is dried with MgSO4 and is filtered. The filtrate is concentrated and the residue is purified by silica gel chromatography eluting with 5% MeOH in CH2Cl2 to afford a less polar product 5-[1-tert-butyl-2-(2-1,2,3-triazol-2-yl-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine (Example 14) (16 mg, 29%) LCMS (ESMS): m/z 411.68 (M++1) as the major product and a more polar product 5-[1-tert-butyl-2-(2-1,2,3-triazol-1-yl-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine (Example 15) (7 mg, 13%) LCMS (ESMS): m/z 411.68 (M++1) as the minor product.

1. temperaturecooled down
2. filtrationfiltered
3. extractionThe filtrate is extracted with H2O (10 mL) and EtOAc (3×10 mL)
4. dry with materialThe combined organic layer is dried with MgSO4
5. filtrationis filtered
6. concentrationThe filtrate is concentrated
7. customthe residue is purified by silica gel chromatography
8. washeluting with 5% MeOH in CH2Cl2