Hydrochloric Acid → HCID 178508527, Verbindung

HRID 895387

Reaktionsgleichung

Reaktionsgleichung von HRID 895387
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:6][N:5]=[C:4]([N:16]=CN(C(C)C)C(C)C)[N:3]=1.Cl.[NH2:26][C@H:27]1[CH2:32][CH2:31][C@H:30]([OH:33])[CH2:29][CH2:28]1.C(N(CC)CC)C.N1C=CC=NC=1.Cl>C(O)C>[NH2:16][C:4]1[N:3]=[C:2]([NH:26][C@H:27]2[CH2:32][CH2:31][C@H:30]([OH:33])[CH2:29][CH2:28]2)[C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)=[CH:6][N:5]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 9260PyrimidineHCID 540285984-Chloro-5-(4-chlorophenoxy)-2-(diisopropylaminomethyleneamino)pyrimidineHCID 178479278HCID 178479278, Verbindung

Produkt 1

HCID 178508527HCID 178508527, VerbindungAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4-Chloro-5-(4-chlorophenoxy)-2-(diisopropylaminomethyleneamino)pyrimidine (3.68 g, 0.01 mole) and trans-4-aminocyclohexanol hydrochloride (5.31 g, 0.035 mole) were combined in absolute ethanol (25 mL). Triethylamine (7.08 g, 0.07 mole) was added, and the mixture was refluxed with stirring for 56 hours when thin layer chromatography confirmed the absence of the starting pyrimidine. The mixture was cooled slightly, concentrated hydrochloric acid (5 mL) was added and reflux was resumed for an additional 2 hours. The mixture was spin evaporated in vacuo. The oily residue was dissolved in water (200 mL) and extracted with dichloromethane (2×200 mL). The aqueous phase was basified with 2 M sodium hydroxide to pH 9, and the gummy residue that precipitated was dissolved in dichloromethane (100 mL). The aqueous phase was back washed with dichloromethane (100 mL), and the combined organic extracts were washed with brine (200 mL), dried over sodium sulfate, filtered and spin evaporated in vacuo to a foam. This material was dissolved in ethyl acetate and chromatographed on Silica Gel 60 (E. M. Science, 230-440 mesh) (8 g; 2×7 cm column bed) using ethyl acetate as eluent. The first 100 mL of eluent was collected and spin evaporated in vacuo to give 2.30 g (69% yield) of 2-amino-5-(4-chlorophenoxy)-4-(trans-4-hydroxycyclohexylamino)pyrimidine as a white powder, mp 154-155° C.

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. temperatureThe mixture was cooled slightly
  3. temperaturereflux
  4. waitwas resumed for an additional 2 hours
  5. customevaporated in vacuo
  6. dissolutionThe oily residue was dissolved in water (200 mL)
  7. extractionextracted with dichloromethane (2×200 mL)
  8. customthe gummy residue that precipitated
  9. dissolutionwas dissolved in dichloromethane (100 mL)
  10. washThe aqueous phase was back washed with dichloromethane (100 mL)
  11. washthe combined organic extracts were washed with brine (200 mL)
  12. dry with materialdried over sodium sulfate
  13. filtrationfiltered
  14. customspin evaporated in vacuo to a foam
  15. dissolutionThis material was dissolved in ethyl acetate
  16. customchromatographed on Silica Gel 60 (E. M. Science, 230-440 mesh) (8 g; 2×7 cm column bed)
  17. customThe first 100 mL of eluent was collected
  18. customspin evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0b3e960019cc49b0a839e93d90c8db64
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06916820B1

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