Triphosgene → 5-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

HRID 271427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271427
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[C:5]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:4]([NH:22][NH2:23])[N:3]=1.Cl[C:25](Cl)([O:27]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[Cl:1][C:2]1[N:3]2[C:25](=[O:27])[NH:23][N:22]=[C:4]2[C:5]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:7]=1

Komponenten

4

Edukt 2

HCID 94429TriphosgeneHCID 587728472-Chloro-4,5-bis(4-chlorophenyl)-6-hydrazinylpyrimidine

Produkt 1

HCID 587728405-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of a mixture of 2-chloro-4,5-bis(4-chlorophenyl)-6-hydrazinylpyrimidine and its regioisomer prepared above (900 mg, 2.46 mmol) in THF (10 mL) at room temperature under argon was added triphosgene (1.46 g, 4.91 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was cooled in an ice bath and carefully quenched with water (10 mL) and then extracted with EtOAc (15 mL×2). The combined organic extracts were washed with water and then saturated aqueous NaCl. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluted with 20% ethyl acetate-hexanes to obtain 400 mg of the title compound as a yellow solid. HPLC/MS: retention time=3.923 min, [M+H]+=391; 1H NMR (DMSO-d6, 500 MHz): δ 12.68 (s, 1H), 7.39 (d, J=8.25 Hz, 2H), 7.31 (d, J=8.25 Hz, 2H), 7.23 (d, J=8.8 Hz, 2H), 7.21 (d, J=8.8 Hz, 2H). Regioisomeric product derived from starting material regioisomeric impurity: HPLC/MS: retention time=3.545 min.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. customcarefully quenched with water (10 mL)
  3. extractionextracted with EtOAc (15 mL×2)
  4. washThe combined organic extracts were washed with water
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by silica gel column chromatography
  9. washeluted with 20% ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-13ee661313fb46ee81f49edec0619a4e
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452892B2

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