Benzyl Alcohol → 4-(benzyloxy)-N-(4-(oxazol-5-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

tert-Butyl-4-hydroxy-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.2 g, 0.49 mmol, Example 3d), phenylmethanol (0.063 ml, 0.61 mmol) and triphenylphosphine (0.160 g, 0.61 mmol) in THF (5 mL) was stirred for 10 min. Diisopropyl azodicarboxylate (0.119 mL, 0.61 mmol) was added and reaction was stirred at 50° C. over night. HCl (2M aq, 2 mL) was added and the solution was heated to 75° C. for 1 h, allowing THF to evaporate. The remaining solvent was evaporated under reduced pressure. The crude product was dissolved in MeOH/DMSO and purified on preparative HPLC to give 4-(benzyloxy)-N-(4-(oxazol-5-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (0.089 g, 39.7%).

Provenance & Evidence