Ethyl bromoacetate → Ethyl 3,6-dihydro-3-(methoxymethyl)-5-nitro-2,6-dioxo-1(2H)-pyrimidineacetate

HRID 397008

Reaktionsgleichung

Reaktionsgleichung von HRID 397008
[N+:1]([C:4]1[C:5](=[O:14])[NH:6][C:7](=[O:13])[N:8]([CH2:10][O:11][CH3:12])[CH:9]=1)([O-:3])=[O:2].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[N+:1]([C:4]1[C:5](=[O:14])[N:6]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7](=[O:13])[N:8]([CH2:10][O:11][CH3:12])[CH:9]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 2

HCID 7748Ethyl bromoacetateHCID 181724885-Nitro-1-methoxymethyluracil

Produkt 1

HCID 21355699Ethyl 3,6-dihydro-3-(methoxymethyl)-5-nitro-2,6-dioxo-1(2H)-pyrimidineacetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 2724141Tetrabutylammonium FluorideLösungsmittel

Versuchsvorschrift

The compound of example 41 (10.0 g, 50 mmole) is dissolved in tetrabutylammonium flouride (120 mL of a 1.0M solution in tetrahydrofuran, 0.124 mole). Ethyl bromoacetate (8.3 mL, 75 mmole) is added. The reaction is stirred at room temperature. The reaction mixture is concentrated, then partitioned between dichloromethane and water. The aqueous layer is extracted with dichloromethane. The combined organic extracts are washed with water, brine, and dried over anhydrous magnesium sulfate. The solvent is removed under vacuum to afford the title compound.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated
  2. custompartitioned between dichloromethane and water
  3. extractionThe aqueous layer is extracted with dichloromethane
  4. washThe combined organic extracts are washed with water, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent is removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-96a36b6cadd045c68beeb6ee26e579cb
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608204B1

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