Cesium carbonate → {[3-(3,4-dimethoxybenzyl)-1-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-6-yl]oxy}acetonitrile

HRID 1022514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022514
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=2)[N:9]([CH:19]2[CH2:24][CH2:23][S:22](=[O:26])(=[O:25])[CH2:21][CH2:20]2)[C:8]1=[O:27].Br[CH2:34][C:35]#[N:36].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH2:34][C:35]#[N:36])[CH:14]=2)[N:9]([CH:19]2[CH2:20][CH2:21][S:22](=[O:26])(=[O:25])[CH2:23][CH2:24]2)[C:8]1=[O:27]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 667326983-(3,4-dimethoxybenzyl)-1-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-6-hydroxyquinazoline-2,4(1H,3H)-dione

Produkt 1

HCID 49764282{[3-(3,4-dimethoxybenzyl)-1-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-6-yl]oxy}acetonitrileAusbeute 72,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 0.055 g of the compound obtained in Step 18.2, 0.017 g of bromoacetonitrile and 0.078 g of Cs2CO3 in 2 ml of DMF is irradiated in a microwave field for 15 minutes at 100° C. The reaction mixture is evaporated under reduced pressure. The residue is taken up in DCM, washed with water, dried over Na2SO4 and filtered, and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with an MeOH/DCM mixture from (0.5/99.5, v/v) to (5/95, v/v), to give 0.043 g of the expected product.

Aufarbeitung

  1. customis irradiated in a microwave field for 15 minutes at 100° C
  2. customThe reaction mixture is evaporated under reduced pressure
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe filtrate is evaporated under reduced pressure
  7. customThe residue is chromatographed on silica gel
  8. washeluting with an MeOH/DCM mixture from (0.5/99.5

Quellen und Nachweise

ORD-Eintrag
ord-3d0d3137c00342a9bdab733d57de377f
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722659B2

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