Methanol → 2-Tert-butyl-4-[(3-methoxypropyl)amino]-6-oxo-1,6-dihydropyrimidine-5-carboxylic acid

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Reaction Conditions

Reaction Steps

Methyl 2-cyano-3-[(2,2-dimethylpropanoyl)amino]-3-(methylsulfanyl)prop-2-enoate (2.0 g) was dissolved in 3-methoxypropan-1-amine (1.4 g), and the mixture was stirred at 80° C. for 1 hr. Methanol (10 ml) was added to the reaction mixture, and the mixture was refluxed overnight. The solvent was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography. The fraction eluted with ethyl acetate-hexane (0:10→6:4) was concentrated under reduced pressure, and the fraction eluted with ethyl acetate was concentrated under reduced pressure. The residue (1.0 g) was dissolved in methanol (10 ml), lithium hydroxide (0.42 g) and water (2 ml) were added, and the mixture was stirred at 70° C. for 6 hr. The reaction mixture was allowed to cool to room temperature, acidified with 6 N aqueous hydrochloric acid solution, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object compound (0.51 g).

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