tert-Butyl 4-oxopiperidine-1-carboxylate → Tert-butyl 4-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylene)piperidine-1-carboxylate

Participants

Reaction Steps

To a suspension of dimethyl (2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylphosphonate from Example 117 (0.71 g) in anhydrous THF (15 mL) at 0° C. was added 2.0 M of lithium diisopropylamide in THF (1.4 eq). The resulting solution was allowed to warm to RT (room temperature) before adding a solution of 1-boc-4-piperidone (1.4 eq) in anhydrous THF (3 mL). The reaction mixture was stirred at room temperature for 1 h, then partitioned between brine and DCM. The organic layer was isolated, dried (MgSO4), concentrated and recrystallized from methanol. The light yellow solid was filtered and collected to give 0.72 g of tert-butyl 4-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylene)piperidine-1-carboxylate as a light yellow solid.

Provenance & Evidence