Process for the preparation of 9-deazaguanine derivatives

Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...

Reexamination Certificate

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C548S532000

Reexamination Certificate

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06946554

ABSTRACT:
Derivatives of 9-deazaguanine of the formula I:are prepared by reacting an aldehyde or ketone of the formula II:with a dialkylaminomalonate to produce an enamine. The enamine is then reacted with a base to produce a pyrrole represented by the formula:The pyrrole is reacted with a compound represented by the formula R3OC(O)N═C(Z)NHC(O)OR3or a derivative of carbamimidoic acid to provide a protected guanidine compound. The guanidine compound is converted to the desired deazaguanine by reaction with 1) trifluoracetic acid or 2) C1-C4alkoxide or alkali metal or alkaline earth metal hydroxide followed by neutralization with an acid.

REFERENCES:
patent: 5554615 (1996-09-01), Nomura et al.
patent: 6043365 (2000-03-01), McQuire et al.

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