Hydrochloric Acid → HCID 15790246, compound

Temperature

15 °C

5-Fluoro-4-hydrazino-2-methoxypyrimidine (15.81 g, 0.100 mol), 47 g of methanol, 10.2 g (0.100 mol) of triethylamine, and 11.4 g (0.15 mol) of carbon disulfide were combined in a 250 mL flask under nitrogen at ambient temperature with stirring to obtain a yellow, heterogeneous mixture. The mixture was cooled to 15° C. with an ice bath. Hydrogen peroxide (12.5 g of 30 percent aqueous, 0.11 mol) was then added by means of a syringe pump, the syringe of which was inserted into the flask through a septum. The addition was made over a 1-hour period with stirring and cooling to maintain the temperature at about 15° C. The mixture was allowed to react and warm for 1 hour and the resulting heterogeneous orange mixture was vacuum filtered to remove the solid sulfur. The filtrate was cooled in an ice bath and acidified with 17.6 mL (0.11 mol) of 6.25N hydrochloric acid diluted with 125 mL of water. The resulting precipitate was recovered by vacuum filtration and dried under reduced pressure to obtain 18.81 g (94 percent of theory) of the title compound as an off-white solid melting at 166° C. with decomposition.

1. customto obtain a yellow, heterogeneous mixture
2. additionThe addition
3. waitwas made over a 1-hour period
4. stirringwith stirring
5. temperaturecooling
6. temperatureto maintain the temperature at about 15° C
7. customto react
8. temperaturewarm for 1 hour
9. filtrationfiltered
10. customto remove the solid sulfur
11. temperatureThe filtrate was cooled in an ice bath
12. filtrationThe resulting precipitate was recovered by vacuum filtration
13. customdried under reduced pressure

ORD record

ord-2774b66e6db94a01880e76901134b894

Source dataset

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05563269