Labelled compounds of interest as antitumour agents – VIII. Synthesis of 2H‐isotopomers of pentamethylmelamine and of a potential prodrug thereof

Treatment of 2‐chloro‐4,6‐(dimethylamino)‐1,3,5‐triazine with trideuteromethylamine gave 4,6‐(dimethylamino)‐2‐trideuteromethyl‐1,3,5‐triazine, an isotopomer of the experimental anticancer agent pentamethylmelamine (PMM). Mitsunobu coupling with 1,2‐dimethyl‐3‐hydroxymethyl‐5‐methoxy‐indole‐4,7‐dione gave 1,2‐dimethyl‐3‐(N‐(4,6‐bis(dimethylamino)‐1,3,5‐triazin‐2‐yl)‐N‐trideuteromethylaminomethyl)‐5‐methoxyindole‐4,7‐dione. This conjugate is a potential reductively triggered prodrug of PMM. Copyright © 2002 John Wiley & Sons, Ltd.