Reacción #497860

Ecuación de reacción

N-{3-[2-(1,1-Dioxido-3,6-dihydro-2H-thiopyran-4-yl)-1,3-thiazol-5-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine

N-{3-[2-(1,1-dioxido-3,6-dihydro-2H-thiopyran-4-yl)-1,3-thiazol-5-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine

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title compound

Rendimiento 72.9%

N-{3-[2-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1,3-thiazol-5-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine

Rendimiento 72.9%

Disolventes

MeOH EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction was flushed with hydrogen (3×)
2. 2
   FiltraciónThe reaction was filtered through a pad of Celite
3. 3
   Concentraciónconcentrated under reduced pressure

Procedimiento

N-{3-[2-(1,1-Dioxido-3,6-dihydro-2H-thiopyran-4-yl)-1,3-thiazol-5-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine (Example 135, 100 mg, 0.214 mmol) was dissolved in a 1:2 v/v mixture MeOH/EtOH (15 mL). Palladium on carbon (57.0 mg, 0.054 mmol) was added, and the reaction was flushed with hydrogen (3×). The reaction was stirred under hydrogen atmosphere at room temperature for 72 hrs. The reaction was filtered through a pad of Celite and concentrated under reduced pressure. Column chromatography on silica (gradient elution, 0 to 75% EtOAc in hexanes) afforded the title compound (0.073 g, 0.156 mmol, 72% yield) as a colorless foam. MS ESI: [M+H]+ m/z 469.0. 1H NMR (500 MHz, DMSO-d6) δ 10.27 (s, 1H), 8.83 (d, J=4.9, 1H), 7.99 (m, 2H), 7.45 (bs, 1H), 7.28 (d, J=4.9, 1H), 7.16 (bs, 1H), 3.43 (m, 1H), 3.34 (m, 2H), 3.18 (m, 2H), 2.39 (m, 2H), 2.26 (s, 3H), 2.31 (m, 2H). rhSYK activity=+++.

Fuente