Hydrochloric Acid → 2-amino-5-fluoro-6-furan-2-yl-3H-pyrimidin-4-one

HRID 1355861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1355861
C([O:3][C:4](=O)[CH:5]([F:13])[C:6]([C:8]1[O:9][CH:10]=[CH:11][CH:12]=1)=O)C.C(=O)(O)O.[NH2:19][C:20]([NH2:22])=[NH:21].Cl>C(O)C.O>[NH2:21][C:20]1[NH:22][C:4](=[O:3])[C:5]([F:13])=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[N:19]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 286947Carbonic acid-guanidine (1:1)HCID 45080919Ethyl 2-fluoro-3-(furan-2-yl)-3-oxopropanoate

Produkt 1

HCID 1357249952-amino-5-fluoro-6-furan-2-yl-3H-pyrimidin-4-oneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Following the method of Skulnick and Wierenga (Patent WO 86/04583), a mixture of 8.72 g (43.6 mmol) (RS)-2-fluoro-3-furan-2-yl-3-oxo-propionic acid ethyl ester and 8.89 g (49.3 mmol) guanidine carbonate in 30 ml ethanol was heated at 100° C. for 16 hours. The reaction mixture was then cooled to 0° C. and diluted with 100 ml water. 1M hydrochloric acid was added dropwise until the mixture was ca pH 3, whereupon the resulting crystals were collected by filtration and washed sequentially with water and with ether to afford 6.11 g (72%) 2-amino-5-fluoro-6-furan-2-yl-3H-pyrimidin-4-one as a brown crystalline solid. EI-MS m/e (%): 95 (M+, 100), 154 ([M—MeCN]+, 24).

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. filtrationwhereupon the resulting crystals were collected by filtration
  3. washwashed sequentially with water and with ether

Quellen und Nachweise

ORD-Eintrag
ord-211b3959d7364457bb7dfdc95f29578c
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586441B2

Notizen zur Reaktion

Wird geladen…