Potassium Carbonate → HCID 178462824, compound

To the solution of (1-ethyl-1H-imidazol-5-yl)methanol (1.26 g, 10 mmol) in dioxane (50 mL) in a 250 mL round bottom flask, was added NCS (1.38 g, 10 mmol). The resulting mixture was stirred at room temperature overnight. Dioxane was removed under vacuum, and the crude solid was dissolved in chloroform (40 mL), followed by addition of PBr3 (1.9 mL, 20 mmol). The resulting mixture was stirred at room temperature overnight. The solvent was then evaporated. The crude 5-(bromomethyl)-4-chloro-1-ethyl-1H-imidazole was dissolved in DMF (20 mL). Potassium carbonate (3 g) and 6-methyl-2-sulfanylpyrimidin-4-ol (1.4 g, 10 mmol) were added. The mixture was stirred at room temperature for 2 hours. DMF was removed under vacuum, and the residue was purified by column chromatography to provide 2-{[(4-chloro-1-ethyl-1H-imidazol-5-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (100 mg, 3% overall yield); 1H NMR (400 MHz, CD3OD): δ 1.41 (t, 3H), 2.29 (s, 3H), 4.12 (q, 1H), 4.60 (s, 2H), 4.59 (m, 1H), 6.01 (br, 1H), 7.66 (s, 1H); M+ 285.

1. customDioxane was removed under vacuum
2. dissolutionthe crude solid was dissolved in chloroform (40 mL)
3. stirringThe resulting mixture was stirred at room temperature overnight
4. customThe solvent was then evaporated
5. dissolutionThe crude 5-(bromomethyl)-4-chloro-1-ethyl-1H-imidazole was dissolved in DMF (20 mL)
6. stirringThe mixture was stirred at room temperature for 2 hours
7. customDMF was removed under vacuum
8. customthe residue was purified by column chromatography

ORD record

ord-88604c3d5fae430599fd4ea170dda59a

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040538B2