Selenium Dioxide → 5-Isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-formyl-2-morpholin-4-yl-pyrimidin-4-ylamide

HRID 356652Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 356652
[Cl:1][C:2]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:3]=1[O:4][C:5]1[C:6]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][N:23]=2)(=[O:21])=[O:20])=[N:7][C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[N:9][C:10]=1[CH3:11].[Se](=O)=[O:38]>O1CCOCC1>[Cl:1][C:2]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:3]=1[O:4][C:5]1[C:6]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][N:23]=2)(=[O:21])=[O:20])=[N:7][C:8]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[N:9][C:10]=1[CH:11]=[O:38]

Komponenten

4

Edukt 2

HCID 24007Selenium DioxideHCID 223778355-Isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-methyl-2-morpholin-4-yl-pyrimidin-4-ylamide

Produkt 1

HCID 223778605-Isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-formyl-2-morpholin-4-yl-pyrimidin-4-ylamideAusbeute 51,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1 g of the compound obtained in Example 36 and 2.1 g of selenium dioxide in 40 ml of dioxan were stirred in an autoclave at 170° C. for 7 hours. The reaction mixture was filtered and the filtrate was concentrated. The residue was partitioned between ethyl acetate and water. The organic phase was dried, the solvent was evaporated and the residue was purified over silica gel with ethyl acetate/hexane. 0.53 g of 5-isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-formyl-2-morpholin-4-yl-pyrimidin-4-ylamide, m.p. 194° C., was obtained.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic phase was dried
  5. customthe solvent was evaporated
  6. customthe residue was purified over silica gel with ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-c3b639ff2c404d589f278cae338f982e
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05837708

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