Triethylamine → 1-(2,4-Dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-amine

HRID 1628770

Reaktionsgleichung

Reaktionsgleichung von HRID 1628770
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2=[N:15][C:16]3[C:17](=[C:18](C(O)=O)[CH:19]=[CH:20][CH:21]=3)[N:13]2[CH2:12][CH2:11][CH2:10]1.C1(P(C2C=CC=CC=2)(=O)O)C=CC=CC=1.C([N:42](CC)CC)C>C(O)(C)(C)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2=[N:15][C:16]3[C:17](=[C:18]([NH2:42])[CH:19]=[CH:20][CH:21]=3)[N:13]2[CH2:12][CH2:11][CH2:10]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 15567Diphenylphosphinic acidHCID 577864031-(2,4-Dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylic acid

Produkt 1

HCID 577861701-(2,4-Dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylic acid (9.40 g, 25.9 mmol), diphenylphosphinic acid (7.85 g, 28.5 mmol) and triethylamine (4.0 mL) in t-butanol (250 mL) was stirred at 90° C. for 12 hr and concentrated in vacuo. A mixture of the residue and trifluoroacetic acid (100 mL) in dichloromethane (50 mL) was stirred at room temperature for 20 hr and concentrated in vacuo. The residue 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. The residue was purified by flash column chromatography on silica gel eluting with a 10-60% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound as a yellow amorphous (440 mg, 1.32 mmol, 5%).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionA mixture of the residue and trifluoroacetic acid (100 mL) in dichloromethane (50 mL)
  3. stirringwas stirred at room temperature for 20 hr
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with saturated aqueous sodium hydrogen carbonate
  6. extractionextracted with ethyl acetate
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-60% ethyl acetate/n-hexane gradient mixture
  12. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5443908838cb4432a944a6e38444d03f
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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