4,6-Dichloro-2-(methylsulfonyl)pyrimidine → 2,6-Difluoro-N-[4-(4,6-dichloro-pyrimidin-2-ylsulfanyl)-phenyl]-benzamide

Temperatur

90 °C

A 250 ml round bottom flask equipped with a condenser was charged with 4,6-dichloro-2-methanesulfonyl pyrimidine (4.2 g, 18.8 mmol), 2,6-difluoro-N-(4-mercapto-phenyl)-benzamide (4.98 g, 18.8 mmol) and tert-butanol (75 ml) under nitrogen. The reaction mixture was degassed thoroughly and then heated at 90° C. for 2 h. The reaction mixture was allowed to cool to room temperature and concentrated in vacuo. The solid residue was taken up in ethyl acetate (50 ml) and washed with saturated sodium bicarbonate solution and brine. The organic was dried over magnesium sulfate, filtered and concentrated until the product began to precipitate. The mixture was then cooled and aged for 12 hrs. The product was collected by filtration, washed with cold ethyl acetate and dried. This gave the title compound as an off-white solid (2.7 g, 35%). 1H NMR (DMSO) 7.32 (2H, m), 7.61 (3H, m), 7.79 (1H, s), 7.82 (2H, d), 10.9 (1H, s). MS (ES+): 412.19

1. customA 250 ml round bottom flask equipped with a condenser
2. customThe reaction mixture was degassed thoroughly
3. temperatureto cool to room temperature
4. concentrationconcentrated in vacuo
5. washwashed with saturated sodium bicarbonate solution and brine
6. dry with materialThe organic was dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated until the product
9. customto precipitate
10. temperatureThe mixture was then cooled
11. filtrationThe product was collected by filtration
12. washwashed with cold ethyl acetate
13. customdried

ORD-Eintrag

ord-1c16a2205d114a86b2d46a396d619f44

Quelldatensatz

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08637511B2