Ammonia → 4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid amide

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Reaction Steps

To a solution of 200 mg of 4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid (Example 13) (0.515 mmol) in 5 ml of DMF was added 235 mg of HATU (0.618 mmol) and 0.4 ml of N,N-diisopropylethyl amine. Let stir at rt for 30 min. Added 2.1 ml of 0.5 M NH3 in dioxane (1.03 mmol) dropwise over 5 min. Let stir overnight added 0.5 eq. of 0.5M NH3 in dioxane (0.5 ml). Added EtOAc and 1N NaOH until pH=9 and washed with 10% citric acid, sat'd NaHCO3 and brine. Dried over NaSO4 and conc'd in vacuo to afford 80.9 mg (40%) of pure product (MH+=388.34).

Provenance & Evidence