Cl[C:2]1[C:7]([F:8])=[C:6]([Cl:9])[N:5]=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[N:3]=1.C(NC(C)C)(C)C.[CH3:21][C:22]1[CH:26]=[C:25]([NH2:27])[NH:24][N:23]=1>C1COCC1.C(OCC)(=O)C.O>[Cl:9][C:6]1[N:5]=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[N:3]=[C:2]([NH:27][C:25]2[NH:24][N:23]=[C:22]([CH3:21])[CH:26]=2)[C:7]=1[F:8]
To a solution of 4,6-dichloro-5-fluoro-2-(methylsulfonyl)pyrimidine in THF (25 ml) was added diisopropylamine (1.32 g, 10.20 mmol, 1.82 ml) and 3-methyl-1H-pyrazol-5-amine (1.04 g, 10.71 mmol) and the mixture stirred at room temperature for 30 mins. The reaction was diluted with ethyl acetate (100 ml) and water (100 ml), the organic layer was washed with brine (50 ml), dried (Na2SO4), and partially concentrated until a solid started to precipitate. The suspension was cooled in an ice bath for 1 hr and filtered to give the title compound as a pale yellow solid. A second crop was obtained by leaving the filtrate to stand overnight (total 1.55 g, 50%). 1H NMR (DMSO, 400 MHz) 2.26 (3H, s), 3.32 (3H, s), 6.48 (1H, s), 11.03 (1H, s), 12.35 (1H, s) ES+ 306.
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