1,3-Dibromopropane → 4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 349555

Reaktionsgleichung

Reaktionsgleichung von HRID 349555
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]#[N:8].C(N(CC)CC)C.Br[CH2:17][CH2:18][CH2:19]Br>O1CCOCC1>[N:5]1[N:6]2[CH2:17][CH2:18][CH2:19][NH:1][C:2]2=[C:3]([C:7]#[N:8])[CH:4]=1

Komponenten

5

Edukt 3

HCID 80011,3-DibromopropaneHCID 8471TriethylamineHCID 855155-Amino-4-cyanopyrazole

Produkt 1

HCID 1356713724,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a solution of 5-aminopyrazole-4-carbonitrile (102 g) and triethylamine (316 ml) in 1,4-dioxane (2000 ml) was added 1,3-dibromopropane (115 ml), and the mixture was stirred at 95° C. for 5 days. The insoluble materials were removed by filtration, and the filtrate was concentrated in vacuo. To the residue was added 10% aqueous citric acid solution, and the mixture was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with 2-propanol and dried in vacuo to give 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (8.0 g) as a solid.

Aufarbeitung

  1. customThe insoluble materials were removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionTo the residue was added 10% aqueous citric acid solution
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with 2-propanol
  9. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-912c718fea374522827ed71adc7db813
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179801B2

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