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

HRID 1278229

Reaction equation

HRID 1278229 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8164944684734bd5a5356bb8e83c1ee0
Source dataset
uspto-grants-1981_07
Patent number
US04281000

Linked notes

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