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Water → 1-(4-(6-(N-Methyl-N-phenylamino)pyrimidin-4-yloxy)phenyl)-3-phenylurea

HRID 853529
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 853529
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:17])=[CH:11][CH:10]=2)[CH:3]=1.[CH3:25][NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(OCC)(=O)C.O>CN1CCCC1=O.CCCCCC>[CH3:25][N:26]([C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:17])=[CH:11][CH:10]=2)[CH:3]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 7515N-MethylanilineHCID 8857Ethyl Acetate2×HCID 22937019N-(4-(6-Chloropyrimidin-4-yloxy)phenyl)-N'-phenylurea

Produkt 1

HCID 229370001-(4-(6-(N-Methyl-N-phenylamino)pyrimidin-4-yloxy)phenyl)-3-phenylureaAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8058
Hexane
Lösungsmittel
HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

N-(4-(6-Chloropyrimidin-4-yloxy)phenyl)-N′-phenylurea (68.0 mg, 0.200 mmol) and N-methylaniline (107 mg, 1.00 mmol) were heated and stirred in 1-methylpyrrolidone (1 ml) at 130° C. for 36 hours. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent—ethyl acetate:hexane=1:1), the fraction containing the target substance was concentrated and suspended in ethyl acetate, the suspension was diluted with hexane and the crystals were filtered out, washed with hexane and blow-dried to obtain the title compound (38 mg, 0.092 mmol, 46%) as colorless crystals.

Aufarbeitung

  1. washthe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered off
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe obtained crude product
  6. additionthe fraction containing the target substance
  7. concentrationwas concentrated
  8. additionthe suspension was diluted with hexane
  9. filtrationthe crystals were filtered out
  10. washwashed with hexane
  11. customblow-dried

Quellen und Nachweise

ORD-Eintrag
ord-3994f839bb63456eb91eaeedadc76691
Quelldatensatz
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07253286B2

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