Diethyl fluoromalonate → HCID 178517898, Verbindung

Sodium hydride (60% in oil, 3.9 g, 96.5 mmol) was washed with hexanes in a round bottom flask under argon and cooled with an ice water bath. EtOH (100 mL) was slowly added. The resulting mixture was warmed to RT and stirred for 30 minutes. To the base mixture, diethyl 2-fluoromalonate (5.7 g, 32.2 mmol) was added, followed by morpholinoformamidine hydrobromide (6.8 g, 32.2 mmol). The mixture was heated to 90-95° C. with stirring under argon. After 12 hours, the reaction was cooled to room temperature and the EtOH was removed in vacuo. The resulting white solid was dissolved in water (25 mL) and acidified with conc. HCl to pH=3-4. A white precipitate formed which was collected on a Büchner filter, washed with water (2×50 mL), air dried on the filter, and dried in vacuo to give 5-fluoro-2-morpholinopyrimidine-4,6-diol (0.87 g, 12%). LC/MS (m/z): 216.0 (MH+), Rt 0.63 minutes.

1. temperaturecooled with an ice water bath
2. temperatureThe mixture was heated to 90-95° C.
3. stirringwith stirring under argon
4. waitAfter 12 hours
5. temperaturethe reaction was cooled to room temperature
6. customthe EtOH was removed in vacuo
7. dissolutionThe resulting white solid was dissolved in water (25 mL)
8. customA white precipitate formed which
9. customwas collected on a Büchner
10. filtrationfilter
11. washwashed with water (2×50 mL), air
12. customdried on the filter
13. customdried in vacuo

ORD-Eintrag

ord-4cdc23db2d4a4eec9fc2588a575711f2

Quelldatensatz

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08217035B2