Propargyl alcohol → 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-3-(prop-2-yn-1-yloxy)propan-1-one

Participants

Reaction Conditions

Reaction Steps

Add 1,8-diazabicyclo [5.4.0]undec-7-ene (0.035 mL; 0.15 equiv; 0.23 mmoles) to a solution of 1-[2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]prop-2-en-1-one (0.5 g; 1.0 equiv; 1.56 mmoles) and 2-propyn-1-ol (5.0 mL; 55 equiv; 85.86 mmoles). Stir the reaction at ambient temperature for 16 hours, then heat to 50° C. for 36 hours. Concentrate the solution to a brown oil, then purify the crude product by column chromatography (20 to 100% ethyl acetate in dichloromethane) to afford the desired 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-3-(prop-2-yn-1-yloxy)propan-1-one (0.28 g; 48%): MS (m/z): 377 (M+1).

Provenance & Evidence