Dimethyl acetylenedicarboxylate → Methyl 5,6-dihydroxy-2-((1-phenylcyclopentyl)methyl)pyrimidine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of potassium hydroxide (10.8 ml, 10.8 mmol) in methanol and hydroxylamine hydrochloride (10.8 ml, 10.8 mmol) in methanol were mixed, filtered and added to 2-(1-phenylcyclopentyl)acetonitrile (1 g, 5.4 mmol) in methanol (MeOH) and stirred at 60° C. for 24 h. It was then evaporated to dryness. The residue was dissolved in chloroform (30 ml) and to this was added dimethyl but-2-ynedioate (844 mg, 5.94 mmol). The reaction mixture was The mixture was stirred at 60° C. for 24 h, cooled and evaporated to dryness. The residue was dissolved in xylene (10 ml) and heated at 140° C. in a microwave oven for 1 h. The cooled residue was evaporated to dryness. Chromatography was conducted (40 g SiO2; 10 to 70% EtOAc in hexanes). The residue was triturated with EtOAc, filtered and washed with Et2O and dried under vacuum to give the title product as an off-white solid (0.110 g; 6%). LCMS: m/z=329 (MH+).

Provenance & Evidence