Hydrochloric Acid → HCID 59311385, compound

2-Amino-4,6-dichloropyrimidine-5-carbaldehyde (100 g) was suspended in tetrahydrofuran (4000 ml), and a 1 N solution of vinylmagnesium bromide in tetrahydrofuran (2200 g) was added dropwise under ice-cooling. After completion of the dropwise addition, the mixture was stirred under ice-cooling for two hours. Water (2000 ml) was added to the reaction solution, and the solution was made acidic with a 1 N hydrochloric acid solution (2500 ml), followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and filtered, followed by concentration. Methanol was added to the resulting residue, followed by stirring for one hour. The insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-chloroform) to obtain the title compound (50 g, 49%) as a solid.

1. temperaturecooling
2. additionAfter completion of the dropwise addition
3. temperaturecooling for two hours
4. extractionfollowed by extraction with ethyl acetate
5. dry with materialThe organic layer was dried over sodium sulfate
6. filtrationfiltered
7. concentrationfollowed by concentration
8. additionMethanol was added to the resulting residue
9. stirringby stirring for one hour
10. filtrationThe insoluble matter was filtered off
11. concentrationthe filtrate was concentrated under reduced pressure
12. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-chloroform)

ORD record

ord-06c0bf9ed94e4a92b579485c47e72460

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158638B2