Hydrochloric Acid → 1-[3,3-bis(methyloxy)propyl]-5-(4-isothiazolyl)-2,4(1H,3H)-pyrimidinedione

HRID 1925027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1925027
Cl.[S:2]1[CH:6]=[C:5]([C:7]2[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][CH:12]=2)[CH:4]=[N:3]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][CH2:23][CH:24]([O:27][CH3:28])[O:25][CH3:26].Cl>CN(C)C=O.O>[CH3:26][O:25][CH:24]([O:27][CH3:28])[CH2:23][CH2:22][N:11]1[CH:12]=[C:7]([C:5]2[CH:4]=[N:3][S:2][CH:6]=2)[C:8](=[O:14])[NH:9][C:10]1=[O:13]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 67519670HCID 67519670, Verbindung

Produkt 1

HCID 594483771-[3,3-bis(methyloxy)propyl]-5-(4-isothiazolyl)-2,4(1H,3H)-pyrimidinedioneAusbeute 13,44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-(4-isothiazolyl)-2,4(1H,3H)-pyrimidinedione hydrochloride (Prep23, 300 mg, 1.036 mmol) was dissolved in N,N-Dimethylformamide (DMF) (4 ml) to give a pale yellow suspension. K2CO3 (215 mg, 1.554 mmol) was added ant the reaction mixture was stirred at room temperature for 1 h. 3-bromo-1,1-bis(methyloxy)propane (0.173 ml, 1.140 mmol) was added. Mixture was stirred at room temperature for 3 days, then diluted with water, acidified with diluted HCl until pH ˜5, and extracted with EtOAc. The organic phase was washed with water (3 times), brine, dried over Na2SO4, filtered and the solvent evaporated. The obtained residue was purified by flash chromatography eluting with cyclohexane/EtOAc 1:1. Obtained 60 mg (13.44% yield) of a 9:1 mixture of the title compound and the corresponding bis alkylated derivative.

Aufarbeitung

  1. customto give a pale yellow suspension
  2. stirringMixture was stirred at room temperature for 3 days
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with water (3 times), brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe obtained residue was purified by flash chromatography
  9. washeluting with cyclohexane/EtOAc 1:1
  10. customObtained

Quellen und Nachweise

ORD-Eintrag
ord-e6711f020bb345af8d423ef606e16fde
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178549B2

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