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Chloroform → 4-(4-(4-Acetyl-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile

HRID 1805878
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1805878
[C:1]([C:4]1[CH:35]=[C:34]([CH3:36])[C:7]([O:8][C:9]2[C:10]3[N:26](CC4C=CC=CC=4)[CH:25]=[CH:24][C:11]=3[N:12]=[C:13]([NH:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[N:14]=2)=[C:6]([CH3:37])[CH:5]=1)(=[O:3])[CH3:2].[Al+3].[Cl-].[Cl-].[Cl-].C(Cl)(Cl)Cl>ClC1C=CC=CC=1Cl>[C:1]([C:4]1[CH:5]=[C:6]([CH3:37])[C:7]([O:8][C:9]2[C:10]3[NH:26][CH:25]=[CH:24][C:11]=3[N:12]=[C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:20]#[N:21])=[CH:22][CH:23]=3)[N:14]=2)=[C:34]([CH3:36])[CH:35]=1)(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6212ChloroformHCID 6451240Aluminum(III) ChlorideHCID 576936424-(4-(4-Acetyl-2,6-dimethylphenoxy)-5-benzyl-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile

Produkt 1

HCID 119624034-(4-(4-Acetyl-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrileAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7239
1,2-Dichlorobenzene
Lösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a suspension of 4-(4-(4-acetyl-2,6-dimethylphenoxy)-5-benzyl-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile (65 mg, 0.13 mmol) in 1,2-dichlorobenzene (5.3 mL) was added AlCl3 (178 mg, 1.3 mmol). The reaction mixture was heated at 160° C. for 1.5 h, after which time the reaction mixture became dark and homogeneous. Upon completion of the reaction, the reaction mixture was cooled, CHCl3 was added, and the mixture was washed with NH4Cl. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel column chromatography, eluting with hexanes:ethyl acetate (3:1), to give the product as a brown solid (41 mg, 77%).

Aufarbeitung

  1. customUpon completion of the reaction
  2. temperaturethe reaction mixture was cooled
  3. washthe mixture was washed with NH4Cl
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel column chromatography
  9. washeluting with hexanes:ethyl acetate (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-e14db315f8bf4100b31ebd6c36042a65
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08354532B2

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