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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 915959Erstellt: 26. Oktober 2026

Tetrahydrofuran → 3-Cyclohexyl-6-[2-methoxy-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

https://huagongshe.com/reaction/915959

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTetrahydrofuranHCID 8028—
Edukt2-Chloroethyl chloroformateHCID 12305—
EduktSodium BicarbonateHCID 516892—
Edukt6-(4-Amino-2-methoxyphenyl)-3-cyclohexyl-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-oneHCID 135948887—
LösungsmittelTriethylamineHCID 8471—
Produkt3-Cyclohexyl-6-[2-methoxy-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-oneHCID 13600587365%

Reaktionsschritte

To a 6 ml tetrahydrofuran solution of 150 mg (0.425 mmol) of the compound obtained in Example 44, 79 μl (0.765 mmol) of 2-chloroethyl chloroformate and triethylamine were added, and the mixture was stirred at room temperature for 20 hours. Further, 30 μl (0.29 mmol) of 2-chloroethyl chloroformate was added, and the mixture was stirred at room temperature for 4 hours. Then, an aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. After the washed layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. To a 2 ml ethanol solution of the residue, 1 ml of a 1M aqueous solution of sodium hydroxide was added, and the mixture was stirred at room temperature for 5 hours. Then, the reaction mixture was neutralized with a 1M aqueous solution of hydrochloric acid, and extracted with chloroform. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. After the washed layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol to obtain 116 mg (65%) of the captioned compound.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07268128B2
Quelldatensatzuspto-grants-2007_09
ORD IDord-87c775a0fec840318451c5ca000e20f9
Quellennotizuspto-grants-2007_09