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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 2072852Erstellt: 24. Oktober 2026

Diethyl Ether → 2,5-Methano-5H,9H-pyrimido(2,1-b)(1,5,3)dioxazepin-9-one, 2,3-dihydro-3-(hydroxymethyl)-8-methyl-, (2R,3R,5R)-

https://huagongshe.com/de/reaction/2072852

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktDiethyl EtherHCID 3283—
EduktDiphenyl carbonateHCID 7597—
Edukt5-MethyluridineHCID 445408—
KatalysatorSodium BicarbonateHCID 516892—
LösungsmittelMethanolHCID 887—
LösungsmittelDimethylformamideHCID 6228—
Produkt2,5-Methano-5H,9H-pyrimido(2,1-b)(1,5,3)dioxazepin-9-one, 2,3-dihydro-3-(hydroxymethyl)-8-methyl-, (2R,3R,5R)-HCID 457982101,4%

Reaktionsbedingungen

Temperatur150 °C

Reaktionsschritte

A 100 mL round bottom flask equipped with magnetic stir bar, reflux condensor, and nitrogen inlet was charged with 5 g of ribothymidine, 4.7 g (1.2 eq) of diphenyl carbonate and 150 mg of sodium bicarbonate in 10 mL of DMF. The mixture was heated to 150° C. for 35 minutes. The black solution was diluted with 10 mL of MeOH and slowly added to 200 mL of diethyl ether. The tan product was filtered and dried to yield 4.4 g (96%) of anhydrothymidine.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS04914233
Quelldatensatzuspto-grants-1990_04
ORD IDord-c0b3691bde8f4128a9160c5ebc5206ac
Quellennotizuspto-grants-1990_04