METHOD OF PRODUCING PYRIMIDINYLCYCLOPENTANE COMPOUNDS Russian patent published in 2024 - IPC C07D239/70 C07C269/06 C07C271/22 A61K31/517 

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing a compound of formula (I)

or salts thereof, involving a coupling reaction of a compound of formula (II)

with a compound of formula (III)

where R¹ is an amino-protective group selected from the list: benzyl, benzyloxycarbonyl (carbobenzyloxy, CBZ), 9-fluorenylmethyloxycarbonyl (Fmoc), p-methoxybenzyloxycarbonyl, p-nitrobenzyloxycarbonyl, tert-butoxycarbonyl (BOC) and trifluoroacetyl, R² is an amino-protective group selected from the list: benzyl, benzyloxycarbonyl (carbobenzyloxy, CBZ), 9-fluorenylmethyloxycarbonyl (Fmoc), p-methoxybenzyloxycarbonyl, p-nitrobenzyloxycarbonyl, tert-butoxycarbonyl (BOC) and trifluoroacetyl, M is an alkali metal ion; further comprising the following reaction steps: a) deprotection of the compound of formula (III) in a solvent under acidic conditions; b) bringing to alkaline pH with a base; c) adding a solution containing a compound of formula (II) to a solvent; d) adding a solution containing a coupling agent to a solvent; wherein the deprotection in step a) is carried out using hydrochloric acid, sulfuric acid, trifluoroacetic acid or hydrobromic acid and the solvent is selected from water, methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol; base at step b) is selected from N-ethylmorpholine (NEM), triethylamine (TEA), tri (n-propyl) amine (TPA), diisopropylethylamine (DIPEA), pyridine and lutidine; solvent used in step c) is selected from water, methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol and the coupling agent used in step d) is propylphosphonic anhydride (T3P).

EFFECT: improved method of obtaining compounds of formula (I), which provides better stereoselectivity, which eliminates the need for subsequent chiral chromatography, requires fewer reaction steps, provides higher output.

69 cl, 5 tbl, 16 ex