Hydrochloric Acid → 2,2,2-Trifluoro-1-[9-methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]ethanol

HRID 1629022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1629022
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([CH:44]=[O:45])=[C:25]2[C:29]=1[N:28]=[C:27]1[N:30]([C:34]3[C:35]([CH3:43])=[N:36][C:37]([O:41][CH3:42])=[N:38][C:39]=3[CH3:40])[CH2:31][CH2:32][CH2:33][N:26]21.C[Si](C)(C)[C:48]([F:51])([F:50])[F:49].Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[F:49][C:48]([F:51])([F:50])[CH:44]([C:24]1[C:25]2[N:26]3[CH2:33][CH2:32][CH2:31][N:30]([C:34]4[C:35]([CH3:43])=[N:36][C:37]([O:41][CH3:42])=[N:38][C:39]=4[CH3:40])[C:27]3=[N:28][C:29]=2[C:21]([O:20][CH3:19])=[CH:22][CH:23]=1)[OH:45]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 577857769-Methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde

Produkt 1

HCID 441565002,2,2-Trifluoro-1-[9-methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]ethanolAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran, 0.13 mL, 0.13 mmol) was added to a stirred solution of the 9-methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde (467 mg) and trimethyl(trifluoromethyl)silane (361 mg, 2.54 mmol) in tetrahydrofuran (5.0 mL) at 0° C., and the mixture was stirred at 0° C. for 30 min, at room temperature for 70 min. 1N Hydrochloric acid (5.0 mL) was added to the mixture at room temperature, and the mixture was stirred for 15 min. The mixture was neutralized with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 0-7% methanol/ethyl acetate gradient mixture. The eluate was concentrated in vacuo to give the title compound as a colorless solid (224 mg, 0.512 mmol).

Aufarbeitung

  1. stirringthe mixture was stirred for 15 min
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 0-7% methanol/ethyl acetate gradient mixture
  8. concentrationThe eluate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-68a06d3f79374136ae09bbaf6f958d43
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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