Water → 1-(3,3-Dimethoxy-propyl)-5-(6-fluoro-pyridin-2-yl)-1H-pyrimidine-2,4-dione

HRID 12705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 12705
Cl.[F:2][C:3]1[N:8]=[C:7]([C:9]2[C:10](=[O:16])[NH:11][C:12](=[O:15])[NH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][CH:26]([O:29][CH3:30])[O:27][CH3:28].O>CN(C=O)C>[CH3:28][O:27][CH:26]([O:29][CH3:30])[CH2:25][CH2:24][N:13]1[CH:14]=[C:9]([C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([F:2])[N:8]=2)[C:10](=[O:16])[NH:11][C:12]1=[O:15]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 686903145-(6-Fluoro-pyridin-2-yl)-1H-pyrimidine-2,4-dione hydrochloride

Produkt 1

HCID 589942011-(3,3-Dimethoxy-propyl)-5-(6-fluoro-pyridin-2-yl)-1H-pyrimidine-2,4-dioneAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5-(6-Fluoro-pyridin-2-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep75, 200 mg, 0.82 mmol), and K2CO3 (169 mg, 1.23 mmol) in DMF (4 ml) was stirred 1 hour at room temperature. 3-Bromo-1,1dimethoxy-propane (165 mg, 0.90 mmol) was added and stirring was continued for 48 hours. Water (50 ml) was added and the product was extracted with ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was triturated with iPr2O to give 179 mg of the final compound as a white solid (70% yield).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 48 hours
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe crude was triturated with iPr2O

Quellen und Nachweise

ORD-Eintrag
ord-e9f8b59231f648d7990315cef63ab5fc
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727988B2

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