Benzyl Chloride → [9-Chloro-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]acetonitrile

HRID 1399134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1399134
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:14]2[N:13]=[C:12]3[N:15]([C:19]4[C:20]([CH3:28])=[N:21][C:22]([O:26][CH3:27])=[N:23][C:24]=4[CH3:25])[CH2:16][CH2:17][CH2:18][N:11]3[C:10]=2[C:9]([CH2:29]O)=[CH:8][CH:7]=1.[C-:31]#[N:32].[Na+].C(Cl)C1C=CC=CC=1>O1CCCC1.C(=O)([O-])O.[Na+].O.CS(C)=O.N1C=CC=CC=1>[Cl:5][C:6]1[C:14]2[N:13]=[C:12]3[N:15]([C:19]4[C:20]([CH3:28])=[N:21][C:22]([O:26][CH3:27])=[N:23][C:24]=4[CH3:25])[CH2:16][CH2:17][CH2:18][N:11]3[C:10]=2[C:9]([CH2:29][C:31]#[N:32])=[CH:8][CH:7]=1

Komponenten

10

Edukt 4

HCID 7503Benzyl ChlorideHCID 8929Sodium CyanideHCID 24386Thionyl ChlorideHCID 57786330[9-Chloro-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol

Produkt 1

HCID 57786008[9-Chloro-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]acetonitrileAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Thionyl chloride (0.56 mL, 7.65 mmol) was added to a stirred solution of [9-chloro-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol (1.43 g, 3.83 mmol) and pyridine (0.10 mL) in tetrahydrofuran (20 mL) at 0° C., and the mixture was stirred at 0° C. for 30 min. The mixture was diluted 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. A solution of sodium cyanide (375 mg, 7.65 mmol) in water (1.0 mL) was added to the resulting benzyl chloride in dimethylsulfoxide (20 mL), and the mixture was stirred at room temperature for 14 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and the precipitate was collected by filtration, washed with diisopropyl ether to give the title compound as a colorless powder (1.42 g, 3.71 mmol, 97% in 2 steps).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. stirringthe mixture was stirred at room temperature for 14 hr
  7. filtrationthe precipitate was collected by filtration
  8. washwashed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-b2b5b88f5bfd41958bb54eb2046af3c3
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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