Water → 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-yloxy)ethanone

Participants

Reaction Steps

Add sodium hydride (0.054 g; 1.85 equiv; 1.35 mmoles) to a solution of 5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ol (0.252 g; 2.0 equiv; 1.46 mmoles) in dimethylformamide (2 mL) and stir at room temperature for 10 minutes. Add this mixture to a 0° C. solution of 2-chloro-1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]ethanone (0.25 g; 1.0 equiv; 0.729 mmoles) in dimethylformamide (2 mL). Stir the resulting solution at 0° C. for 1 hour, then add water and load onto a SCX ion exchange column. Elute off the crude product (methanol to 7N ammonia in methanol). Further purify the product by reverse phase chromatography to afford 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-yloxy)ethanone (0.035 g; 11%) as a white foam. MS (m/z): 445(M+1).

Provenance & Evidence