3-amino-5-methyl-1H-pyrazole-4-carbonitrile → 2-Methyl-7-(3-pyridyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 1278228

Reaktionsgleichung

Reaktionsgleichung von HRID 1278228
C[N:2]([CH3:13])[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=O.[NH2:14][C:15]1[C:19](C#N)=[C:18]([CH3:22])[NH:17][N:16]=1>C(O)(=O)C>[CH3:22][C:18]1[C:19]([C:15]#[N:14])=[C:13]2[N:2]=[CH:3][CH:4]=[C:5]([C:7]3[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=3)[N:16]2[N:17]=1

Komponenten

4

Edukt 2

HCID 2274603-amino-5-methyl-1H-pyrazole-4-carbonitrileHCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one

Produkt 1

HCID 112648292-Methyl-7-(3-pyridyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 3.50 g. of 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one, 25 L ml. of glacial acetic acid and 2.44 g. of 3-amino-5-methylpyrazole-4-carbonitrile is refluxed 6 hours. The solvent is removed in vacuo. The residue is dissolved in dichloromethane and the solution washed with saturated sodium bicarbonate solution. The dichloromethane layer is dried over anhydrous sodium sulfate and pased through a column of hydrous magnesium silicate. The eluent is concentrated and hexane added to give 2.60 g. of the product of the example, m.p. 245°-246° C.

Aufarbeitung

  1. additionA mixture of 3.50 g
  2. customThe solvent is removed in vacuo
  3. dissolutionThe residue is dissolved in dichloromethane
  4. washthe solution washed with saturated sodium bicarbonate solution
  5. dry with materialThe dichloromethane layer is dried over anhydrous sodium sulfate
  6. concentrationThe eluent is concentrated
  7. additionhexane added
  8. customto give 2.60 g

Quellen und Nachweise

ORD-Eintrag
ord-1a3027a6c96b43e18745f0fae0541f4f
Quelldatensatz
uspto-grants-1981_07
Patentnummer
US04281000

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