3-amino-1H-pyrazole-4,5-dicarbonitrile → 3-Cyano-7-(alpha,alpha,alpha-trifluoro-m-tolyl)pyrazolo-[1,5-a]pyrimidine-2-carbonitrile

HRID 225269Notes

Reaction equation

HRID 225269 reaction equation
C[N:2]([CH3:17])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)=O.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.[NH2:42][C:43]1[C:47](C#N)=[C:46]([C:50]#[N:51])[NH:45][N:44]=1>>[C:43]([C:47]1[C:46]([C:50]#[N:51])=[N:45][N:44]2[C:5]([C:7]3[CH:8]=[C:9]([C:13]([F:14])([F:15])[F:16])[CH:10]=[CH:11][CH:12]=3)=[CH:4][CH:3]=[N:2][C:17]=12)#[N:42]

Participants

4

Reactant 3

HCID 3388303-amino-1H-pyrazole-4,5-dicarbonitrileHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 7300243-Dimethylamino-3'-trifluoromethylacrylophenone

Product 1

HCID 113704003-Cyano-7-(alpha,alpha,alpha-trifluoro-m-tolyl)pyrazolo-[1,5-a]pyrimidine-2-carbonitrile

Procedure

A mixture of 4.86 g. of 3-dimethylamino-3'-(trifluoromethyl)acrylophenone, 50 ml. of glacial acetic and 2.66 g. of 3-aminopyrazole-4,5-dicarbonitrile is refluxed for 10 hours and the solvent removed under reduced pressure. The residue is reacted with trifluoroacetic anhydride to give the product of the example.

Workup

  1. additionA mixture of 4.86 g
  2. customthe solvent removed under reduced pressure
  3. customThe residue is reacted with trifluoroacetic anhydride
  4. customto give the product of the example

Sources & evidence

ORD record
ord-8a041eab68fa4b0f9476f8937d90c71f
Source dataset
uspto-grants-1980_11
Patent number
US04236005

Reaction notes

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