Water → 1-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione

HRID 12665

Reaktionsgleichung

Reaktionsgleichung von HRID 12665
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][CH:12]=1.[H-].[Na+].I[CH2:18][CH2:19][CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].O>CN(C=O)C>[C:26]([Si:23]([CH3:24])([CH3:25])[O:22][CH2:21][CH2:20][CH2:19][CH2:18][N:11]1[CH:12]=[C:7]([C:3]2[S:4][CH:5]=[CH:6][C:2]=2[CH3:1])[C:8](=[O:14])[NH:9][C:10]1=[O:13])([CH3:29])([CH3:28])[CH3:27]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 4250746tert-Butyl(4-iodobutoxy)dimethylsilaneHCID 149145925-(3-Methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione

Produkt 1

HCID 691349881-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dioneAusbeute 23,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione (Prep 26, 250 mg, 1.2 mmol) in DMF (10 mL), 60% NaH (58 mg, 1.44 mmol) was added portionwise. The reaction was then heated to 70° C. and this temperature was maintained for 1.5 hour. After cooling to room temperature, (4-iodo-butoxy)-tert-butyl-dimethyl-silane (452 mg, 1.44 mmol) was then added dropwise and the reaction was stirred for 24 hours. Water (30 mL) was added and the product was extracted with Et2O. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (15-85) followed by DCM/MeOH (70:30) to give the title compound as a yellow oil (110 mg, 23% yield).

Aufarbeitung

  1. temperaturethis temperature was maintained for 1.5 hour
  2. temperatureAfter cooling to room temperature
  3. extractionthe product was extracted with Et2O
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe crude was purified by flash chromatography with ethyl acetate-petroleum ether (15-85)

Quellen und Nachweise

ORD-Eintrag
ord-f8276ed10f254d9d97d0a20aa58f09dd
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727988B2

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