Process for preparing mkc-442

Details Process for preparing mkc-442 Process for preparing mkc-442

C - Chemistry, Metallurgy

07

D

C07D 239/54 (2006.01)

Patent

CA 2369698

A process for preparing 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil, which is also known as MKC-442, is disclosed. The process comprises synthesizing an isopropyl ~-ketoester, such as ethyl-2-isopropyl-3-oxo-4-phenyl-butyrate, using any known method, including from benzyl cyanide and ethyl-2-bromo-3,3- dimethyl-propionate with activated zinc in a Reformatsky reaction. The ethyl-2- isopropyl-3-oxo-4-phenyl-butyrate is then condensed with thiourea in one of two ways. First, the ethyl-2-isopropyl-3-oxo-4-phenyl-butyrate is condensed with thiourea in a two-base system in the presence of a solvent. A second process for condensing the ethyl-2-isopropyl-3-oxo-4-phenyl-butyrate with thiourea is conducted in the presence of potassium t-butoxide to form a benzyl isopropyl thiouracil, which is desulfurized in process step (B). The benzyl isopropyl uracil resulting from either process is then alkoxyalkylated in process to form MKC-442.

L'invention concerne un procédé de préparation de 6-benzyl-1-(éthoxyméthyl)-5-isopropyluracil, appelé MKC-442. Ce procédé consiste à faire la synthèse d'un isopropyl ß-cétoester, notamment un éthyl-2-isopropyl-3-oxo-4-phényl-butyrate, grâce au procédé connu consistant à inclure un phénylacétonitrile et éthyl-2-bromo-3,3-diméthyl-propionate avec un zinc activé dans une réaction Reformatsky. L'éthyl-2-isopropyl-3-oxo-4-phényl-butyrate est condensé par la suite avec une thiourée de deux manières. D'après la première, l'éthyl-2-isopropyl-3-oxo-4-phényl-butyrate est condensé avec la thiourée dans un système à double base en présence d'un solvant et d'après la seconde, il est condensé avec une thiourée en présence d'un potassium t-butoxyde afin d'obtenir un benzyl isopropyl thiouracil, qui est désulfuré à l'étape (B). Le benzyl isopropyl uracil obtenu est soumis à une alcoxyalkylation afin d'obtenir un MKC-442.

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