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Synthesis of [2-14C]dezaguanine mesylate (6-amino-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one-6-14C methanesulfonate), a new antitumor agent

✍ Scribed by Jon D. Hartman; Vitauts Alks; C. C. Huang; P. Dan Cook

Publisher
John Wiley and Sons
Year
1986
Tongue
French
Weight
385 KB
Volume
23
Category
Article
ISSN
0022-2135

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✦ Synopsis

Dezaguanine mesylate (CI-908 mesylate, 3deazaguanine mesylate, 6amino-1,5-dihydro-4H-imidazo[4,5~_]pyridin-4-one methanesulfonate, 71, a new a n t itumor agent, w a s l a b e l e d in t h e 2 -p o s i t i o n by use of a new s y n t h e s i s t o 3deazaguanine. imidazole-S-carboxylate (10) was converted w i t h t h i o n y l c h l o r i d e t o t h e corresponding chloromethyl d e r i v a t i v e 2, which was t r e a t e d w i t h [ 14C]potassium cyanide t o a f f o r d t h e l a b e l e d penultimate intermediate, methyl 5-(cyanomethyl)-1H-imidazole-4-carboxylate (12).

methanolic ammonia and subsequent s a l t formation provided [2-14C]3Tdeazaguanine mesylate (13).

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