(e)-3-(4-Chlorophenyl)-n-[1-(2,2-diethoxyethyl)-2-oxo-1,2-dihydropyrimidin-4-yl]-acrylamide → (e)-3-(4-Chloro-phenyl)-n-[1-(2,2-dihydroxy-ethyl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acrylamide

HRID 1425648

Reaktionsgleichung

Reaktionsgleichung von HRID 1425648
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][C:13]2[CH:18]=[CH:17][N:16]([CH2:19][CH:20]([O:24]CC)[O:21]CC)[C:15](=[O:27])[N:14]=2)=[O:11])=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][C:13]2[CH:18]=[CH:17][N:16]([CH2:19][CH:20]([OH:24])[OH:21])[C:15](=[O:27])[N:14]=2)=[O:11])=[CH:4][CH:3]=1

Komponenten

3

Edukt 1

HCID 68902508(e)-3-(4-Chlorophenyl)-n-[1-(2,2-diethoxyethyl)-2-oxo-1,2-dihydropyrimidin-4-yl]-acrylamide

Produkt 1

HCID 57959562(e)-3-(4-Chloro-phenyl)-n-[1-(2,2-dihydroxy-ethyl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acrylamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

(E)-3-(4-chloro-phenyl)-N-[1-(2,2-diethoxy-ethyl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acrylamide (c, 2.48 g, 6.8 mM) was dissolved in trifluoroacetic acid (37 mL) and stirred at room temperature for 4.5 hours. Trifluoroacetic acid was removed in vacuo, and toluene (40 mL) was added to remove the solvent in vacuo. The residual solid was added with ethyl acetate (15 mL) and 5% aqueous sodium bicarbonate (15 mL) and stirred at room temperature. The precipitated crystal was filtered to afford 2.28 g of the desired compound (E)-3-(4-chloro-phenyl)-N-[1-(2,2-dihydroxy-ethyl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acrylamide (d) (yield 100%, colorless crystal).

Aufarbeitung

  1. customTrifluoroacetic acid was removed in vacuo, and toluene (40 mL)
  2. additionwas added
  3. customto remove the solvent in vacuo
  4. additionThe residual solid was added with ethyl acetate (15 mL) and 5% aqueous sodium bicarbonate (15 mL)
  5. stirringstirred at room temperature
  6. filtrationThe precipitated crystal was filtered

Quellen und Nachweise

ORD-Eintrag
ord-3afd7c77fb014b4d8dd458b74a24ac23
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933012B2

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