3-amino-5-methyl-1H-pyrazole-4-carbonitrile → 2,6-Dimethyl-7-(3-pyridyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 1278229

Reaktionsgleichung

Reaktionsgleichung von HRID 1278229
C[N:2]([CH3:14])[CH:3]=[C:4]([CH3:13])[C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=O.[NH2:15][C:16]1[C:20](C#N)=[C:19]([CH3:23])[NH:18][N:17]=1>C(O)(=O)C>[CH3:23][C:19]1[C:20]([C:16]#[N:15])=[C:14]2[N:2]=[CH:3][C:4]([CH3:13])=[C:5]([C:7]3[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=3)[N:17]2[N:18]=1

Komponenten

4

Edukt 2

HCID 2274603-amino-5-methyl-1H-pyrazole-4-carbonitrileHCID 543564803-Dimethylamino-2-methyl-1-(3-pyridyl)-2-propen-1-one

Produkt 1

HCID 118175332,6-Dimethyl-7-(3-pyridyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 1.90 g. of 3-dimethylamino-2-methyl-1-(3-pyridyl)-2-propen-1-one and 1.22 g. of 3-amino-5-methylpyrazole-4-carbonitrile in 25 ml. of glacial acetic acid is refluxed for 6 hours. The solvent is removed in vacuo and the residue partitioned between dichloromethane and saturated sodium bicarbonate solution. The dichloromethane layer is separated, dried over anhydrous sodium sulfate and passed through a column of hydrous magnesium silicate. The eluent is concentrated and hexane added to give 0.95 g. of the product of the example, m.p. 207°-209° C.

Aufarbeitung

  1. additionA mixture of 1.90 g
  2. customThe solvent is removed in vacuo
  3. customthe residue partitioned between dichloromethane and saturated sodium bicarbonate solution
  4. customThe dichloromethane layer is separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe eluent is concentrated
  7. additionhexane added
  8. customto give 0.95 g

Quellen und Nachweise

ORD-Eintrag
ord-8164944684734bd5a5356bb8e83c1ee0
Quelldatensatz
uspto-grants-1981_07
Patentnummer
US04281000

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