Sodium periodate → 6-(benzyloxy)-3-(3,4-dimethoxybenzyl)-1-(1-oxidotetrahydro-2H-thiopyran-4-yl)-quinazoline-2,4(1H,3H)-dione

HRID 1022510Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022510
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH:19]1[CH2:24][CH2:23][S:22][CH2:21][CH2:20]1)[C:14](=[O:25])[N:13]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=1)[C:12]2=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:39].[Na+]>CO.CCO.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH:19]1[CH2:24][CH2:23][S:22](=[O:39])[CH2:21][CH2:20]1)[C:14](=[O:25])[N:13]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=1)[C:12]2=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 23667635Sodium periodateHCID 667327516-(benzyloxy)-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-thiopyran-4-yl)quinazoline-2,4(1H,3H)-dione

Produkt 1

HCID 667327356-(benzyloxy)-3-(3,4-dimethoxybenzyl)-1-(1-oxidotetrahydro-2H-thiopyran-4-yl)-quinazoline-2,4(1H,3H)-dioneAusbeute 106,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86664769MeOH EtOH waterLösungsmittel

Versuchsvorschrift

A mixture of 0.9 g of 6-(benzyloxy)-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-thiopyran-4-yl)quinazoline-2,4(1H,3H)-dione and 0.445 g of sodium periodate in 20 ml of an MeOH/EtOH/water mixture (5/5/1, v/v/v) is stirred overnight at room temperature. The resulting mixture is evaporated under reduced pressure. Water is added and the resulting mixture is extracted with DCM. The organic phase is dried over Na2SO4. The resulting mixture is filtered, and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/MeOH mixture from (100/0, v/v) to (95/5, v/v) to give 0.99 g of the expected product.

Aufarbeitung

  1. customThe resulting mixture is evaporated under reduced pressure
  2. additionWater is added
  3. extractionthe resulting mixture is extracted with DCM
  4. dry with materialThe organic phase is dried over Na2SO4
  5. filtrationThe resulting mixture is filtered
  6. customthe filtrate is evaporated under reduced pressure
  7. customThe residue is chromatographed on silica gel
  8. washeluting with a DCM/MeOH mixture from (100/0

Quellen und Nachweise

ORD-Eintrag
ord-42f30d7786f641aa8d3a3cdf412e0be2
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722659B2

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