2-Propen-1-one, 3-(dimethylamino)-1-(4-pyridinyl)- → 2-Methyl-7-(4-pyridinyl)pyrazolo(1,5-a) pyrimidine-3-carbonitrile

HRID 345937

Reaktionsgleichung

Reaktionsgleichung von HRID 345937
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH3:7])[C:3]=1[C:8]#[N:9].CN(C)[CH:12]=[CH:13][C:14]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)=O>C(O)(=O)C>[CH3:7][C:4]1[C:3]([C:8]#[N:9])=[C:2]2[N:1]=[CH:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[N:6]2[N:5]=1

Komponenten

4

Edukt 2

HCID 7145312-Propen-1-one, 3-(dimethylamino)-1-(4-pyridinyl)-HCID 178434678HCID 178434678, Verbindung

Produkt 1

HCID 150420792-Methyl-7-(4-pyridinyl)pyrazolo(1,5-a) pyrimidine-3-carbonitrileAusbeute 52,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 6.1 g of 5-amino-3-methyl-4-pyrazole carbonitrile and 8.81 g of 3-dimethylamino-1-(4-pyridinyl)-2-propen-1-one in 50 ml of glacial acetic acid is stirred and heated at reflux for 5 hours. The reaction mixture is cooled and the precipitate which forms is collected by filtration and washed with water and a little dichloromethane to give a solid. The solid is partitioned between saturated sodium bicarbonate and dichloromethane. The organic layer is dried over anhydrous sodium sulfate and passed through a short column of hydrous magensium silicate. The addition of hexane to the eluate crystallizes the product which is collected by filtration to give 6.17 g of the desired product, mp 220°-221° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationthe precipitate which forms is collected by filtration
  5. washwashed with water
  6. customa little dichloromethane to give a solid
  7. customThe solid is partitioned between saturated sodium bicarbonate and dichloromethane
  8. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  9. additionThe addition of hexane to the eluate
  10. customcrystallizes the product which
  11. filtrationis collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-736be818a20d44ff905cd66d42aed486
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05059691

Verknüpfte Notizen

Wird geladen…