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Ammonia → methyl 3-[2-allyl-6-(methylthio)-3-oxo-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-1-yl]benzoate

HRID 1630373
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1630373
N1C=CC=CC=1.[CH2:7]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[N:13][C:14]([S:20][CH3:21])=[N:15][CH:16]=2)[NH:11]1)[CH:8]=[CH2:9].[CH3:22][O:23][C:24]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)=[O:25].N>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O.C(Cl)(Cl)Cl>[CH2:7]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[N:13][C:14]([S:20][CH3:21])=[N:15][CH:16]=2)[N:11]1[C:30]1[CH:31]=[C:26]([CH:27]=[CH:28][CH:29]=1)[C:24]([O:23][CH3:22])=[O:25])[CH:8]=[CH2:9]
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Komponenten

8

Edukt 4

HCID 222AmmoniaHCID 1049PyridineHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 671714702-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one

Produkt 1

HCID 67171015methyl 3-[2-allyl-6-(methylthio)-3-oxo-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-1-yl]benzoateAusbeute 55,7 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 8895Cupric acetateKatalysatorHCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

20 mL of pyridine was added to a chloroform solution of 7.5 g of 2-allyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one, 6.1 g of copper(II) acetate and 10 g of [3-(methoxycarbonyl)]phenylboronic acid, and stirred at room temperature for 3 days. Aqueous 30% ammonia solution and saturated saline water were added to the reaction liquid in that order, and extracted with chloroform. The organic layer was washed with saturated saline water, then dried with anhydrous magnesium sulfate, and the solvent was evaporated away. The crude product was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain 6.7 g of methyl 3-[2-allyl-6-(methylthio)-3-oxo-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-1-yl]benzoate as a yellow oily substance.

Aufarbeitung

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated saline water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated away
  5. customThe crude product was purified through silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-b749d91ec3cb4cfabad6d2234e0f914b
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08791125B2

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