Trimethylsilyl isocyanate → [4-(4-Chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenyl]-urea

HRID 629010Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629010
C[Si]([N:5]=[C:6]=[O:7])(C)C.[Cl:8][C:9]1[C:14]([S:15][CH3:16])=[C:13]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:12]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)[N:10]=1>C1COCC1>[Cl:8][C:9]1[C:14]([S:15][CH3:16])=[C:13]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:12]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:6]([NH2:5])=[O:7])=[CH:25][CH:24]=2)[N:10]=1

Komponenten

4

Edukt 2

HCID 70696Trimethylsilyl isocyanateHCID 86673495HCID 86673495, Verbindung

Produkt 1

HCID 86673497[4-(4-Chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenyl]-ureaAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Trimethylsilyl isocyanate (136 mg, 5 eq.) was added to a stirred solution of 4-(4-Chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenylamine (80 mg, 0.237 mmol.) in THF (2.0 ml) and the mixture was reacted to reflux for 16 hrs. The reaction mixture was extracted with EA and washed with brine. The crude was purified by Chromatography (Hexane/EtOAc 1:1) to give a product 28.1 mg (31.2%).

Aufarbeitung

  1. customthe mixture was reacted
  2. temperatureto reflux for 16 hrs
  3. extractionThe reaction mixture was extracted with EA
  4. washwashed with brine
  5. customThe crude was purified by Chromatography (Hexane/EtOAc 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-8f3dca6440bc480696c3a6da501d985f
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315491B2

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