Ethyl chloroacetate → Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetate

Temperature

25 °C

Amino-3,5-dibromopyrazine (1 equiv) in dimethylformamide was cooled to 0° C. and treated with cesium carbonate (1.3 equiv) and ethyl chloroacetate (1.2 equiv). The solution was warmed to 25° C. and further heated to 65° C. The reaction mixture was cooled to 25° C., filtered, and the solid was washed with dimethylformamide. The filtrate was added to ice-water and the slurry was agitated. The resulting solid was isolated, washed with water, and dried. The crude product was dissolved in methyl t-butyl ether with heating, cooled to rt, and concentrated to dryness. The solid was dissolved in ethyl acetate and concentrated to a thick slurry. The product was triturated with 2% ethyl acetate in heptane, filtered, washed with heptane, and dried to afford the title compound as a solid. MS (ESI) m/z 337.8 [M−1]+, 339.8 [M+1]+, 341.8 [M+3]+.

1. temperaturefurther heated to 65° C
2. temperatureThe reaction mixture was cooled to 25° C.
3. filtrationfiltered
4. washthe solid was washed with dimethylformamide
5. additionThe filtrate was added to ice-water
6. customThe resulting solid was isolated
7. washwashed with water
8. customdried
9. dissolutionThe crude product was dissolved in methyl t-butyl ether
10. temperaturewith heating
11. temperaturecooled to rt
12. concentrationconcentrated to dryness
13. dissolutionThe solid was dissolved in ethyl acetate
14. concentrationconcentrated to a thick slurry
15. customThe product was triturated with 2% ethyl acetate in heptane
16. filtrationfiltered
17. washwashed with heptane
18. customdried

ORD record

ord-b4c7bba3886942cab3059d2e90797e6d

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359364B2