1,4-Diazabicyclo(2.2.2)octane--trimethylalumane (1/2) → 2-N-Methyl-2-N-phenyl-6-(5-{5H,6H,7H-pyrrolo[3,4-d]pyrimidin-6-yl}-1,2,4-oxadiazol-3-yl)-1,3,5-triazine-2,4-diamine

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Reaction Steps

To a solution of 6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidine hydrochloride salt (38 mg, 0.231 mmol) in anhydrous THF (3 mL) was added DABAL-Me3 (bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]-octane) (57 mg, 0.231 mmol) at room temperature. The solution was heated under nitrogen at 40 C for 3 h and N-methyl-N-phenyl-6-(5-trichloromethyl-[1,2,4]oxadiazol-3-yl)-[1,3,5]triazine-2,4-diamine (Intermediate 60, 60 mg, 0.155 mmol) was added. The resulting reaction mixture was heated at 80 C for 5 h and then quenched with water (2 mL) drop-wise. The solution was extracted into EtOAc (3×25 mL) and the combined organics washed with a 1M aq. solution of HCl (20 mL), brine (20 mL), dried over magnesium sulfate, evaporated to dryness and purified by preparative HPLC-MS (Method B) to afford the title compound as a white solid (5 mg, 8%).

Provenance & Evidence