Cesium carbonate → 2-Chloro-7,7-difluoro-5-methyl-9-(2-phenoxy-ethyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

HRID 1676842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676842
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([F:15])([F:14])[CH2:8][NH:7][C:6]=2[N:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([F:15])([F:14])[CH2:8][N:7]([CH2:24][CH2:25][O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:6]=2[N:16]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 18551759(2-Iodoethoxy)benzeneHCID 866375242-Chloro-7,7-difluoro-5-methyl-5,7,8,9-tetrahydro-6H-pyrimido[4,5-b][1,4]diazepin-6-one

Produkt 1

HCID 866375282-Chloro-7,7-difluoro-5-methyl-9-(2-phenoxy-ethyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-oneAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 0.20 g (0.8 mmole) of 2-chloro-7,7-difluoro-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-292) in 2 mL of dimethylformamide was added 0.53 g (1.6 mmole) of cesium carbonate, followed by 0.8 g (3.2 mole) of (2-iodo-ethoxy)-benzene. After stirring at 50 degrees overnight, the mixture was filtered and then concentrated under reduced pressure. Dichloromethane and saturated sodium carbonate were added. The mixture was extracted twice with dichloromethane. The combined organic layers were washed three times with sodium carbonate, three times with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 0.28 g of 2-chloro-7,7-difluoro-5-methyl-9-(2-phenoxy-ethyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-304) as an oil.

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. additionDichloromethane and saturated sodium carbonate were added
  4. extractionThe mixture was extracted twice with dichloromethane
  5. washThe combined organic layers were washed three times with sodium carbonate, three times with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d353d74f300a4524b87a89577f7c3851
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003785B2

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