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4-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)butane-1,2-diol → 3-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propanal

HRID 2357983
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2357983
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[C:18]2[C:13](=[N:14][C:15]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:16][CH:17]=2)[N:12]([CH2:26][CH2:27][CH:28]([OH:31])CO)[N:11]=1>CC(C)=O.O.C(Cl)Cl>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH:9][C:10]1[C:18]2[C:13](=[N:14][C:15]([NH:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[N:16][CH:17]=2)[N:12]([CH2:26][CH2:27][CH:28]=[O:31])[N:11]=1
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Komponenten

5

Edukt 1

HCID 160488204-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)butane-1,2-diol

Produkt 1

HCID 588368773-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propanal

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 6344Dichloromethane
Lösungsmittel

Versuchsvorschrift

A solution of 114 mg (0.3 mmol) of 4-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)butane-1,2-diol 34 (Example 2) in 10 mL of acetone and 7 mL of water was treated with 585 mg (2.7 mmol) of NaIO4. The resulting tan slurry was stirred at room temperature for 6 h. The reaction mixture was diluted with CH2Cl2, filtered, and the filtrate was concentrated. The residue was dissolved in CH2Cl2 (75 mL) and washed with water (50 mL). The aqueous layer was extracted with more CH2Cl2 (2×75 mL). The combined organic layers were dried over Na2SO4 and filtered, and the filtrate was concentrated to give the title compound 36, which was used without further purification. 1H-NMR (CDCl3) δ 2.27 (s, 6H), 3.05 (t, J=6.7 Hz, 2H), 4.52 (t, J=6.7 Hz, 2H), 5.30 (s, 1H), 5.89 (s, 1H), 7.06 (t, J=7.6 Hz, 1H), 7.13-7.19 (m, 3H), 7.34 (t, J=7.7 Hz, 2H), 7.42 (s, 1H), 7.64 (d, J=7.7 Hz, 2H), 9.89 (s, 1H). Mass Spectrum (ESI) m/e=387.2 (M+1).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in CH2Cl2 (75 mL)
  4. washwashed with water (50 mL)
  5. extractionThe aqueous layer was extracted with more CH2Cl2 (2×75 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-fa1e64e7e4cb4df3bff950d9fae4529f
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07763624B2

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