Acetic Acid → HCID 59333790, compound

Participants

Reaction Steps

N-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-(2-(tetrahydrofuran-2-yl)ethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (0.133 g, 0.31 mmol, Example 114a), formaldehyde (8.43 μL, 0.31 mmol) and acetic acid (8.76 μL, 0.15 mmol) in methanol (4 mL) was stirred at room temperature for 20 minutes. Polymer supported cyanoborohydride (0.46 g, 0.92 mmol) was added and the reaction mixture was stirred at room temperature overnight. The polymer supported cyanoborohyride was filtered off and the filtrated was purified by preparative chromatography. The product containing fractions were pooled and the solvent was evaporated. The residue was dissolved in water/acetonitrile-mixture (50:50) and freezedried giving N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-methyl-4-(2-(tetrahydrofuran-2-yl)ethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (0.055 g, 40.1%).

Provenance & Evidence