Water → N-(3-Methylsulfonylphenyl)-N'-(4-(6-phenylaminopyrimidin-4-yloxy)phenyl)urea

HRID 387992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387992
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=2)=[CH:4][CH:3]=1.C1([O:28][C:29](=O)[NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([S:37]([CH3:40])(=[O:39])=[O:38])[CH:32]=2)C=CC=CC=1.O>CS(C)=O.C(OCC)(=O)C.CCCCCC>[CH3:40][S:37]([C:33]1[CH:32]=[C:31]([NH:30][C:29]([NH:1][C:2]2[CH:21]=[CH:20][C:5]([O:6][C:7]3[CH:8]=[C:9]([NH:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[N:10]=[CH:11][N:12]=3)=[CH:4][CH:3]=2)=[O:28])[CH:36]=[CH:35][CH:34]=1)(=[O:38])=[O:39]

Komponenten

7

Edukt 3

HCID 962WaterHCID 22936234Phenyl 3-methylsulfonylphenylcarbamateHCID 22936405N-(6-(4-Aminophenoxy)pyrimidin-4-yl)phenylamine

Produkt 1

HCID 22936246N-(3-Methylsulfonylphenyl)-N'-(4-(6-phenylaminopyrimidin-4-yloxy)phenyl)ureaAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

N-(6-(4-Aminophenoxy)pyrimidin-4-yl)phenylamine (55.6 mg, 0.200 mmol) and (3-methylsulfonylphenyl)carbamic acid phenyl ester (63.8 mg, 0.220 mmol) were heated and stirred in dimethylsulfoxide (1 ml) at 85° C. for 2 hours. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with 1N aqueous sodium hydroxide, water and saturated saline 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 suspended in ethyl acetate, the suspension was diluted with hexane, and the crystals were filtered out, washed with hexane and then blow-dried to obtain the title compound (77.0 mg, 0.162 mmol, 81%) as colorless crystals.

Aufarbeitung

  1. washthe organic layer was washed with 1N aqueous sodium hydroxide, water and saturated saline
  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. filtrationthe crystals were filtered out
  7. washwashed with hexane
  8. customblow-dried

Quellen und Nachweise

ORD-Eintrag
ord-9ff303bd2a324f929b117d27380c3ab3
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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