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

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Reaction Steps

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.

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