Acetamide,N-(9-((2-(acetyloxy)-1-((acetyloxy)methyl)ethoxy)methyl)-6,9-dihydro-6-oxo-1H-purin-2-yl)- → Ganciclovir

Participants

Reaction Steps

A solution of 838 mg (2.2 mmole) of 2-acetamido-9-(1,3-diacetoxy-2-propoxymethyl)hypoxanthine in 8.5 ml of 40% methylamine (aqueous) was stirred at gentle reflux under N2 for 1 hour. The solution was then cooled and concentrated to dryness. The residual white solid was recrystallized from a minimum volume of H2O containing 2 drops of acetic acid. After standing in the refrigerator, the product was collected on a filter and washed with a small amount of H2O, then acetone. The material was dried under high vacuum at 75° for 3 hours to giive 529 mg (90% based on hydration with 0.75H2O) of white crystals, mp 249°-250° dec. The material was homogeneous by TLC (80:20:2 CHCl3 --MeOH--H2O), and the structure was confirmed by NMR.

Provenance & Evidence