Process for preparing purine nucleosides

Details Process for preparing purine nucleosides Process for preparing purine nucleosides

C - Chemistry, Metallurgy

07

H

C07H 19/00 (2006.01) C07H 19/16 (2006.01)

Patent

CA 2449561

The present invention provides for the preparation .beta.-adenine nucleosides by coupling an adenine derivative containing an unprotected exocyclic amino group at the C-6 position and a blocked arabinofuranosyl derivative, in the presence of a base and solvent. The present invention also provides for the stereoselective preparation of 2-deoxy-.beta.-D-adenine nucleosides wherein a blocked 2-deoxy-.beta.-D-arabinofuranosyl halide is coupled with the salt of an adenine derivative. The forgoing aspects of the present invention are utilized in the preparation of a clofarabine composition wherein the ratio of .beta. to .alpha.-anomer is at least 99:1.

La présente invention concerne un procédé de préparation de nucléosides à .szlig.-adénine par couplage d'un dérivé d'adénine contenant un groupe amino exocyclique non protégé en position C-6 et d'un dérivé d'arabinofuranosyl bloqué, en présence d'une base et d'un solvant. Cette invention se rapporte en outre à un procédé de préparation stéréosélective de nucléosides à 2-déoxy-.szlig.-D-adénine, selon lequel un halogénogure de 2-déoxy-a-D-arabinofuranosyl bloqué est couplé avec le sel d'un dérivé d'adénine. Ces différents aspects de l'invention sont utilisés pour préparer une composition de clofarabine dans laquelle la proportion de .szlig. anomère contre a anomère est d'au moins 99:1.

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