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Water → 7-(Cyclopropylmethyl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7,9-dihydro-8H-purin-8-one

HRID 510139
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 510139
[CH:1]1([CH2:4][N:5]2[C:13]3[C:8](=[N:9][C:10]([C:14]4[C:22]5[C:17](=[N:18][CH:19]=[CH:20][CH:21]=5)[N:16]([CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[F:30])[N:15]=4)=[N:11][CH:12]=3)[N:7](CC3C=CC(OC)=CC=3OC)[C:6]2=[O:42])[CH2:3][CH2:2]1.C([SiH](CC)CC)C.O.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O.C(OCC)(=O)C>[CH:1]1([CH2:4][N:5]2[C:13]3[C:8](=[N:9][C:10]([C:14]4[C:22]5[C:17](=[N:18][CH:19]=[CH:20][CH:21]=5)[N:16]([CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[F:30])[N:15]=4)=[N:11][CH:12]=3)[NH:7][C:6]2=[O:42])[CH2:3][CH2:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 666141447-(Cyclopropylmethyl)-9-(2,4-dimethoxybenzyl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7,9-dihydro-8H-purin-8-one

Produkt 1

HCID 666351437-(Cyclopropylmethyl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7,9-dihydro-8H-purin-8-one
Ausbeute 53,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6422Trifluoroacetic acidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

482 mg (0.70 mmol) of the compound from example 84A were dissolved in 21 ml of trifluoroacetic acid, 817 mg (7.02 mmol) of triethylsilane were added and the mixture was heated to reflux for 18 h. The reaction mixture was admixed with water and ethyl acetate, and neutralized with saturated aqueous sodium hydrogencarbonate solution. The organic phase was dried over sodium sulfate and concentrated on a rotary evaporator. The residue was dried under high vacuum, and purified by means of preparative HPLC (eluent: methanol/water with 0.1% trifluoroacetic acid, gradient 30:70→90:10). 156 mg of the title compound were obtained (53% of theory).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 h
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe residue was dried under high vacuum
  6. custompurified by means of preparative HPLC (eluent: methanol/water with 0.1% trifluoroacetic acid, gradient 30:70→90:10)

Quellen und Nachweise

ORD-Eintrag
ord-b225ebb6893542b0a291fb3cb2ae91f9
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09096592B2

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