Sodium → HCID 178439238, compound

Participants

Reaction Conditions

Reaction Steps

4-Hydroxy-6-ethyl-5-propyl-2-(trifluoromethyl)pyrimidine (1.2 g, 5 mmole) was converted to the sodium salt with sodium methoxide (275 mg). The sodium salt was dissolved in DMF and mixed with 2.8 g (5 mmole) of 5-(4'-bromomethylbiphenyl-2-yl)-1-trityl-1H-tetrazole [U.S. Pat. No. 4,870,186], and the mixture heated at 50° C. for 18 hours. The solvent was evaporated to dryness and the residue was triturated with excess water to give a gum which was extracted into EtoAc. The organic layer was washed with H2O twice, dried over Na2SO4 and evaporated to a thick oil (4 g). One gram of this oil was treated with dry HCl saturated methanol for 3 hours then evaporated to dryness. The residue was triturated with hexane twice and decanted to afford a gum. The rest of the material was treated in the same way to provide a total of 2 g of crude product. Flash chromatography through silica gel and elution with CHCl3 contg. 4% MeOH gave 210 mg of the desired compound as a white solid. TLC, Silica gel (CHCl3 -MeOH-NH4OH,7:3:2%) Rf 0.55 MS (DCI) [M+H]+ 469

Provenance & Evidence