Ethyl Acetate → HCID 178434689, compound

Participants

Reaction Steps

To a solution of sodium hydride (50% w/w dispersion in mineral oil; 0.04 g.) in t-butanol (5 ml.) was added 3-methyl-5-(3-hydroxypropylthio)-1,2,4-triazole (0.17 g.) and 2-methylsulphinyl-4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimidine (0.14 g.) (European patent publication No. 30092). The mixture was heated under reflux for 3 hours and evaporated to dryness. The residue was partitioned between EtOAc and 2N aqueous hydrochloric acid. The acid extract was basified with 2N aqueous sodium hydroxide and extracted with EtOAc. This extract was dried (MgSO4) and evaporated to dryness. The residual gum was purified by preparative thin layer chromatography using EtOAc/MeOH/aqueous ammonia (s.g. 0.880) 6:1:1 v/v/v as eluant. Material isolated from the appropriate band was dissolved in EtOAc, filtered and the filtrate treated with a solution of maleic acid (0.1 g.) in EtOAc to give 3-methyl-5-(3-[4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimid-2-yloxy]propylthio)-1,2,4-triazole hydrogen maleate hemihydrate (0.05 g.), m.p. 157°-161° (decomp.).

Provenance & Evidence