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Acetone → N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-cyclopentylamino-acetamide

HRID 732945
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 732945
[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[C:13]([I:15])[C:12]([O:16][CH3:17])=[CH:11][C:10]=2[CH:18]([CH3:20])[CH3:19])=[CH:6][N:5]=[C:4]([NH:21][C:22](=[O:25])[CH2:23]Cl)[N:3]=1.[CH:26]1([NH2:29])[CH2:28][CH2:27]1.[I-].[K+].[CH3:32][C:33](C)=O>>[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[C:13]([I:15])[C:12]([O:16][CH3:17])=[CH:11][C:10]=2[CH:18]([CH3:20])[CH3:19])=[CH:6][N:5]=[C:4]([NH:21][C:22](=[O:25])[CH2:23][NH:29][CH:26]2[CH2:33][CH2:32][CH2:27][CH2:28]2)[N:3]=1
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Komponenten

5

Edukt 4

HCID 180AcetoneHCID 4875Potassium IodideHCID 69828CyclopropylamineHCID 57839077N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-chloro-acetamide

Produkt 1

HCID 25007306N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-cyclopentylamino-acetamide

Versuchsvorschrift

N-[4-Amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-chloro-acetamide (1.13 g, 2.37 mmol), cyclopropylamine (0.807 g, 9.48 mmol), and potassium iodide (25 mg) were added to 25 mL acetone. The reaction mixture was stirred under nitrogen at room temperature for 20 hours, then diluted with EtOac. The mixture was washed with water and brine, and the organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (8% MeOH/methylene chloride-0.1% NH4OH) to give 15 mg of N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-cyclopentylamino-acetamide, m.p.=176.5-178.0° C., MS (M+H)=526.

Aufarbeitung

  1. additiondiluted with EtOac
  2. washThe mixture was washed with water and brine
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (8% MeOH/methylene chloride-0.1% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-e0051e52aac242d8a43fb4214d56aaf7
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07589090B2

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