Cesium carbonate → 3-(3,4-dimethoxybenzyl)-6-(2-fluoroethoxy)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione

HRID 1022489Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022489
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[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][O:22][CH2:21][CH2:20]2)[C:8]1=[O:25].C([O-])([O-])=O.[Cs+].[Cs+].[F:37][CH:38](O)[CH3:39]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH2:39][CH2:38][F:37])[CH:14]=2)[N:9]([CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:8]1=[O:25]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 193593481-Fluoroethan-1-olHCID 497640233-(3,4-dimethoxybenzyl)-6-hydroxy-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione

Produkt 1

HCID 866647673-(3,4-dimethoxybenzyl)-6-(2-fluoroethoxy)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dioneAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 0.2 g of 3-(3,4-dimethoxybenzyl)-6-hydroxy-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione and 0.32 g of Cs2CO3 in 10 ml of DMF is irradiated in a microwave field for 1 minute at 100° C. 0.169 g of fluoroethanol are then added and the mixture is irradiated in a microwave field for 5 minutes at 140° C. The reaction medium is evaporated under reduced pressure. The residue is taken up in EtOAc and washed with water and then with saturated NaCl solution. The resulting solution is dried over Na2SO4, filtered and evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/EtOAc mixture from (80/20, v/v) to give 0.212 g of the expected product.

Aufarbeitung

  1. customis irradiated in a microwave field for 1 minute at 100° C
  2. customthe mixture is irradiated in a microwave field for 5 minutes at 140° C
  3. customThe reaction medium is evaporated under reduced pressure
  4. washwashed with water
  5. dry with materialThe resulting solution is dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue is chromatographed on silica gel
  9. washeluting with a DCM/EtOAc mixture from (80/20

Quellen und Nachweise

ORD-Eintrag
ord-f9e611d056654ab59ef79cf0a04c77d9
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722659B2

Notizen zur Reaktion

Wird geladen…