Piperazine → 5-Methoxy-4-(piperazin-1-yl)pyrimidine

HRID 1463347

Reaktionsgleichung

Reaktionsgleichung von HRID 1463347
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[C:13]([O:14][CH3:15])=[C:12](Cl)[N:11]=[CH:10][N:9]=1>O>[CH3:15][O:14][C:13]1[C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[N:9][CH:10]=[N:11][CH:12]=1

Komponenten

4

Edukt 2

HCID 4837PiperazineHCID 787204,6-Dichloro-5-methoxypyrimidine2×

Produkt 1

HCID 104201525-Methoxy-4-(piperazin-1-yl)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Piperazine (20 g) was dissolved in water (100 mL) in a Parr bottle and then solid 4,6-dichloro-5-methoxypyrimidine (5.00 g, 27.9 mmole) was added. The mixture was vigorously stirred for 2 h at room temperature during which the 4,6-dichloro-5-methoxypyrimidine dissolved. The stirring bar was removed, catalyst (10% Pd/C, 1.0 g) was added to the turbid solution, and the mixture was then hydrogenated (60 psi, 3 h) at room temperature. The catalyst was filtered off and the filtrate extracted 3 times with CH2Cl2. The CH2Cl2 extracts were dried over Na2SO4 and concentrated in vacuo to give a clear oil which solidified upon standing (3.34 g, 61.7%). This crude product was Kugelrohr distilled (yield 3.24 g), dissolved in acetonitrile, and concentrated HCl was added to precipitate the product as a white powder which was dried in vacuo (4.32 g, 94.0% from crude product, m.p. 219°-221.5° C.).

Aufarbeitung

  1. dissolutiondissolved
  2. customThe stirring bar was removed
  3. additioncatalyst (10% Pd/C, 1.0 g) was added to the turbid solution
  4. customhydrogenated (60 psi, 3 h)
  5. customat room temperature
  6. filtrationThe catalyst was filtered off
  7. extractionthe filtrate extracted 3 times with CH2Cl2
  8. dry with materialThe CH2Cl2 extracts were dried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customto give a clear oil which
  11. distillationdistilled (yield 3.24 g)
  12. dissolutiondissolved in acetonitrile
  13. additionconcentrated HCl was added
  14. customto precipitate the product as a white powder which
  15. customwas dried in vacuo (4.32 g, 94.0% from crude product, m.p. 219°-221.5° C.)

Quellen und Nachweise

ORD-Eintrag
ord-60056f4035764aa8989b051074e39052
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05300506

Verknüpfte Notizen

Wird geladen…