To a suspension of (−)-cis-2-benzylaminocyclohexanemethanol salt of 1-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-sulfonic acid (prepared in Example 195) (6.83 g) in acetonitrile (48 ml) were added pyridine (1.47 ml) and phosphorus oxychloride (3.39 ml) and the resulting mixture was stirred at room temperature for two hours. The reaction solution was added dropwise to ammonia water (28%, 48 ml) that cooled to 0° C. and the mixture was stirred for another ten minutes. To the reaction solution were added water (50 ml) and ethyl acetate (100 ml×2) such that the intended products were extracted into an organic layer. The organic layer was washed with 4% ammonia water (50 ml), saturated saline (20 ml), 1N hydrochloric acid (50 ml×2) and saturated saline (50 ml), dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford the same product as Example 209, (+)-1-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-sulfonamide (4.84 g). UPLC/MS 531 (M+H)/0.87 min. (measurement condition 9)
