Tetrahydrofuran → Ethyl-[5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methanesulfonyl-pyrimidin-4-yl]-amine

HRID 1677249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1677249
[CH2:1]([NH:3][C:4]1[C:9]([CH2:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=2[CH:21]([CH3:23])[CH3:22])=[CH:8][N:7]=[C:6](SC)[N:5]=1)[CH3:2].[CH2:26]1COCC1.O[O:32][S:33]([O-:35])=O.[K+]>O>[CH2:1]([NH:3][C:4]1[C:9]([CH2:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=2[CH:21]([CH3:22])[CH3:23])=[CH:8][N:7]=[C:6]([S:33]([CH3:26])(=[O:35])=[O:32])[N:5]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 59598719Ethyl-[5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methylsulfanyl-pyrimidin-4-yl]-amine

Produkt 1

HCID 59598536Ethyl-[5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methanesulfonyl-pyrimidin-4-yl]-amineAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl-[5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methylsulfanyl-pyrimidin-4-yl]-amine (0.129 g, 0.4 mmol) in 20 mL 1:1H2O/THF was added OXONE® (0.461 g, 0.8 mmol) in 4.0 mL H2O. After 2 hours, 50 mL H2O was added and the mixture was extracted with ethyl acetate, washed with H2O and washed with brine. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give ethyl-[5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methanesulfonyl-pyrimidin-4-yl]-amine (0.131 g, 92%) as a white foam.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with H2O
  3. washwashed with brine
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-aba6776f72ed46a291ad69b68654fe32
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008313B2

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