1,1'-Carbonyldiimidazole → HCID 86726572, compound

Participants

Reaction Conditions

Reaction Steps

Add 1,1′-carbonyldiimidazole (0.51 g; 1.2 equiv; 3.15 mmoles) to a solution of 3-(1H-imidazol-5-yl)propan-1-ol (0.50 g; 1.0 equiv; 2.62 mmoles) in dimethylformamide (8.5 mL) and stir for 1 hour. Slowly add N-(2,3-dihydro-1H-inden-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-amine dihydrochloride hydrate (0.94 g; 1.10 equiv; 2.89 mmoles) to the aforementioned solution. Stir for 16 hours at ambient temperature and then heat to 60° C. for an additional 16 hours. Partition the reaction mixture between water and chloroform and separate the layers. Further extract the aqueous layer with chloroform (2×). Dry the combined organic extracts over magnesium sulfate, filter, and concentrate to a viscous liquid. Purify the crude product by column chromatography (0 to 20% methanol in dichloromethane) to afford 3-(1H-imidazol-5-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate (0.041 g; 4%) as a brown solid: MS (m/z): 405(M+1).

Provenance & Evidence