Ammonia → 2-(2-methoxyphenyl)-1-methyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one

HRID 1172653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172653
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.[CH3:12][N:13]1[C:17]2=[N:18][C:19]([S:22][CH3:23])=[N:20][CH:21]=[C:16]2[C:15](=[O:24])[NH:14]1.N.C(=O)([O-])O.[Na+]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(Cl)(Cl)Cl.CN(C)C=O.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:14]1[C:15](=[O:24])[C:16]2[C:17](=[N:18][C:19]([S:22][CH3:23])=[N:20][CH:21]=2)[N:13]1[CH3:12]

Komponenten

8

Edukt 4

HCID 222AmmoniaHCID 516892Sodium BicarbonateHCID 27339582-Methoxyphenylboronic acidHCID 210980271-Methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-3-ol

Produkt 1

HCID 671713542-(2-methoxyphenyl)-1-methyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-oneAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8895Cupric acetateKatalysatorHCID 1049PyridineLösungsmittelHCID 21754633chloroform N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

280 mg of o-methoxyphenylboronic acid, 320 mg of copper(II) acetate and 0.15 mL of pyridine were added to a chloroform/N,N-dimethylformamide (1/1) solution of 90 mg of 1-methyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one, and stirred at room temperature. Aqueous 28% ammonia solution and saturated sodium hydrogencarbonate solution were added to the reaction liquid, and extracted with chloroform. The crude product was purified through a silica gel column (hexane/ethyl acetate) to obtain 68 mg of 2-(2-methoxyphenyl)-1-methyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one.

Aufarbeitung

  1. extractionextracted with chloroform
  2. customThe crude product was purified through a silica gel column (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-49aeb71e3eb54298bea05ce6a875ed05
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834019B2

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