METHOD FOR PREPARING 4-(1,6-DIHYDRO-6-OXO-2-PYRIMIDINYL)AMINO-BENZONITRILE Russian patent published in 2012 - IPC C07D239/36 C07D239/28

Abstract RU 2458056 C2

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to an improved method for preparing 4-[(1,6-dihydro-6-oxo-2- pyrimidinyl)amino]benzonitrile of formula . wherein R is C_1-4alkyl. The method consists in dealkoxycarbonylation of 4-oxo-1,6-dihydropyrimidinylcarboxylic acid (II) ester with added MX salt in the appropriate inert solvent, wherein M is a metal or ammonium or substituted ammonium, and X is an anion having the nucleophilic properties. The compound of formula (II) is new and can be prepared by the reaction of a guanidine derivative of formula (III) and alkoxymethylene malonic acid ester of the ester (IV) by the following scheme: .

The compound (I) prepared by said method is halogenated to prepare the compound (C) which is used in the reaction with the compound (B) to prepare E-4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile (TMC278) showing antiviral action in case of HIV infection.

EFFECT: method enables producing the high-yield and high-purity end product.

14 cl, 2 ex

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RU 2 458 056 C2

Authors

Skhils Did'E Filipp Rober

Stappers Al'Fred Ehlizabet

Dates

2012-08-10—Published

2006-05-24—Filed