1,1'-Carbonyldiimidazole → 5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ylmethyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

Add 1,1′-carbonyldiimidazole (2.87 g; 1.02 equiv; 17.69 mmoles) to a solution of 5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ylmethanol (2.64 g; 1.00 equiv; 17.35 mmoles) in dichloromethane (30 mL), then stir at 40° C. for 1 hour. Add N-(2,3-dihydro-1H-inden-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-amine dihydrochloride hydrate (6.25 g; 1.05 equiv; 18.21 mmoles) and diisopropylethylamine (9.08 mL; 3.0 equiv; 52.04 mmoles) and maintain the reaction at 40° C. for 4 hours. Load the solution directly onto a diisopropylethylamine treated silica gel column and purify the mixture by column chromatography (0 to 15% methanol in ethyl acetate) to give 5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ylmethyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate (3.32 g; 44%) as a colorless foam. MS (m/z): 431(M+1).

Provenance & Evidence