Ethyl Propionate → HCID 178430505, compound

Participants

Reaction Steps

A mixture of methyl 4-[2-(2-[2,2,2-trifluoroethyl]guanidino)pyrid-6-yloxy]butyrimidate (0.3 g.), ammonium chloride (0.054 g.) and MeOH (5 ml.) was stirred at room temperature for 1 hour. The mixture was treated with the sodium salt of ethyl 2-formylpropionate [prepared from ethylformate (0.37 g.), ethyl propionate (0.51 g.) and a 50% w/w dispersion of sodium hydride in oil (0.5 g.) as in the first part of Example 11] and heated under reflux for 18 hours and then evaporated to dryness. The residue was partitioned between ether and H2O and the aqueous phase acidified to pH 1 and washed with ether. The aqueous phase was neutralised with NaHCO3 and extracted three times with EtOAc, and the combined EtOAc extracts dried and evaporated to dryness. A solution of the residue in acetone was added to a solution of maleic acid in acetone and the precipitate collected and crystallised from aqueous EtOH to give 4-hydroxy-5-methyl-2-(3-[2-(2-[2,2,2-trifluoroethyl]guanidino)pyrid-6-yloxy]propyl)pyrimidine hydrogen maleate (0.1 g.), m.p. 209°-210°.

Provenance & Evidence