Process for the preparation of pyrrolo¬2,3-d|pyrimidines

Details Process for the preparation of pyrrolo¬2,3-d|pyrimidines Process for the preparation of pyrrolo¬2,3-d|pyrimidines

C - Chemistry, Metallurgy

07

D

C07D 513/04 (2006.01) C07D 487/04 (2006.01)

Patent

CA 2338945

4(3H)-X-7H-Pyrrolo[2,3-d]pyrimidines in which X is =O or =NH are prepared by (i) treating a 6-amino-4(3H)-X-pyrimidine with a unsubstituted or substituted 1-nitroalk-1-ene to yield a 6-amino-4(3H)-X-pyrimidine which is substituted in the 5-position by a 1-nitroalk-2-yl group; (ii) converting the 5-(1-nitroalk-2- yl)-6-amino-4(3H)-X-pyrimidine to the corresponding 5-(1-oxoalk-2-yl)-6-amino- 4(3H)-X-pyrimidine; and (iii) removing the elements of water from the 5-(1- oxoalk-2-yl)-6-amino-4(3H)-X-pyrimidine to effect cyclization. A typical embodiment involves treating 2,6-diamino-4(3H)-pyrimidone with 1-nitro-4-(4- ethoxycarbonylphenyl)-I-butene to yield 1-nitro-2-(2,6-diamino 4(3H)- oxopyrimidin-5-yl)-4-(4-ethoxycarbonylphenyl)butane which is then treated sequentially with base and acid, without isolation of the intermediate aldehyde, to form 4-[2-(2-amino-4(3H)-oxo-7H-pyrrolo[2,3-d]pyrimidin-5- yl)ethyl]benzoic acid, a valuable known chemical intermediate for the preparation of N-[4-{2-(2-hydroxy-4-amino-7H-pyrrolo[2,3-d]-pyrimidin-5- yl)ethyl}benzoyl]glutamic acid.

L'invention concerne des 4(3H)-X-7H-pyrrolo[2,3-d]pyrimidines dans lesquels X est =O ou =NH et qui sont préparés (1) par le traitement d'un 6-amino-4(3H)-X-pyrimidine avec un 1-nitroalc-1-ène pour donner 6-amino-4(3H)-X-pyrimidine qui est substitué en position 5- par un groupe 1-nitroalk-2-yle; (2) par la transformation du 5-(1-nitroalk-2-yle)-6-amino-4(3H)-X-pyrimidine en un 5-(1-oxoalk-2-yle)-6-amino-4(3H)-X-pyrimidine correspondant et; (3) par l'évacuation des éléments d'eau du 5-(1-oxoalk-2-yle)-6-amino-4(3H)-X-pyrimidine qui permet d'effectuer la cyclisation. Dans un mode de réalisation type, on traite un 2,6-diamino-4(3H)-pyrimidone avec 1-nitro-4-(4-éthoxycarbonylphényle)-l-butène pour obtenir 1-nitro-2-(2,6-diamino-4(3H)-oxopyrimidin-5-yle)-4-(4éthoxycarbonylphényl)butane, qui est ensuite traité avec des bases et des acides sans isolation d'aldéhyde intermédiaire pour former un acide 4-[2-(2-amino-4(3h)-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl)éthyle] benzoïque, intermédiaire chimique connu et apprécié qui sert à la préparation de l'acide N-[4-{2-(2-hydroxy-4-amino-7H-pyrrolo[2,3-d]-pyrimidine-5-yl)éthyl}benzoyl]glutamique.

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