Water → HCID 135829374, compound

Participants

Reaction Steps

To a solution of 4-ethylthiobenzyl alcohol (3.7 g) in tetrahydrofuran (80 mL) were added triethylamine (3.0 mL) and methanesulfonyl chloride (1.7 mL) at 0° C., and the mixture was stirred for 30 minutes. After the insoluble material was removed by filtration, the filtrate was added to a suspension of sodium hydride (60%, 0.88 g) and methyl acetoacetate (2.4 mL) in 1,2-dimethoxyethane (100 mL), and the mixture was heated under reflux for 4 hours. The reaction mixture was poured into saturated aqueous sodium bicarbonate solution, and the mixture was extracted with diethyl ether. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed to give methyl 2-(4-ethylthiobenzyl)-acetoacetate (6.1 g). To a suspension of acetoamidine hydrochloride (0.80 g) in methanol (15 mL) was added sodium methoxide (28% solution in methanol, 1.7 mL), and the mixture was stirred for 5 minutes at room temperature. To the reaction mixture was added a solution of methyl 2-(4-ethylthiobenzyl)-acetoacetate (1.5 g) in methanol (5 mL), and the mixture was stirred for 18 hours at room temperature. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. To the residue was added ethyl acetate, and the resulting precipitated crystals were collected by filtration and dried to give 5-(4-ethylthiobenzyl)-2,6-dimethyl-3H-pyrimidin-4-one (0.33 g).

Provenance & Evidence