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Synthesis of N-hydroxymethylpentamethylmelamine (ring 14C), a cytotoxic-alkylating metabolite of hexamethylmelamine

✍ Scribed by Mark E. Sanders; Matthew M. Ames

Book ID
102371617
Publisher
John Wiley and Sons
Year
1984
Tongue
French
Weight
235 KB
Volume
21
Category
Article
ISSN
0022-2135

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✦ Synopsis

The 14C-ring l a b e l e d c a r b i n o l a m i n e N-hydroxymethylpentamethylmelamine, a m e t a b o l i t e o f t h e c l i n i c a l l y u s e f u l a n t i c a n c e r agent hexamethylmelamine, was prepared i n good y i e l d from c y a n u r i c c h l o r i d e ( r i n g , 2,4,6,-14C).

Amination o f c y a n u r i c c h l o r i d e w i t h dimeth 1 ami ne gave 2-chl oro-4,6-bi s ( dimet h y l ami no)-1,3 ,!i-tri a z i ne-2,4,6-74C. F u r t h e r amination w i t h anhydrous methylamine gave p e n t amet hy 1 me1 arni ne-2,4,6 -14C.

Condens a t i on o f pent amet hy 1 met hy 1 -me1 ami ne w i t h excess aqueous formaldehyde gave N-hydroxymethyl pentamethylmelamine i n 54% o v e r a l l y i e l d .

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