Sodium Iodide → 1-(2-Amino-4,6-dichloropyrimidin-5-yl)-3-buten-1-ol

Indium powder (45.81 g) was added to a mixture composed of 2-amino-4,6-dichloropyrimidine-5-carboaldehyde (63.83 g) and N,N-dimethylformamide (500 mL). Then, sodium iodide (99.66 g) was added at an internal temperature of 10° C. under cooling in an ice bath. Allyl bromide (67.5 mL) was added to the resulting mixture over 20 minutes. After confirming that the internal temperature once increased was decreased, the ice bath was removed and the mixture was stirred for two hours. The reaction mixture was concentrated to about 200 mL under reduced pressure. Then, ethyl acetate (1.5 L) and a saturated sodium bicarbonate solution (1 L) were added to the residue, followed by stirring. The mixture was filtered through Celite and the filtrate was separated. Then, the organic layer was sequentially washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and filtered. Then, the filtrate was concentrated to about 150 mL under reduced pressure. Hexane was added to the resulting residue, followed by stirring. Then, the solid was collected by filtration to obtain the title compound (57.24 g, 74%) as a solid.

1. temperatureunder cooling in an ice bath
2. temperatureonce increased
3. customthe ice bath was removed
4. concentrationThe reaction mixture was concentrated to about 200 mL under reduced pressure
5. additionThen, ethyl acetate (1.5 L) and a saturated sodium bicarbonate solution (1 L) were added to the residue
6. stirringby stirring
7. filtrationThe mixture was filtered through Celite
8. customthe filtrate was separated
9. washThen, the organic layer was sequentially washed with water and brine
10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
11. filtrationfiltered
12. concentrationThen, the filtrate was concentrated to about 150 mL under reduced pressure
13. additionHexane was added to the resulting residue
14. stirringby stirring
15. filtrationThen, the solid was collected by filtration

ORDレコード

ord-862b2b09702c4f4287e4d8fc7bae9615

出典データセット

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08158638B2