3-Dimethylamino-2-methyl-3'-(trifluoromethyl)acrylophenone → 6-Methyl-7-(alpha,alpha,alpha-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 1447864

Reaction equation

HRID 1447864 reaction equation
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[CH:5][NH:4][N:3]=1.CN(C)[CH:11]=[C:12]([CH3:25])[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1)=O>C(O)(=O)C>[CH3:25][C:12]1[CH:11]=[N:1][C:2]2[N:3]([N:4]=[CH:5][C:6]=2[C:7]#[N:8])[C:13]=1[C:15]1[CH:16]=[C:17]([C:21]([F:22])([F:23])[F:24])[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 545299423-Dimethylamino-2-methyl-3'-(trifluoromethyl)acrylophenoneHCID 178510443HCID 178510443, compound

Product 1

HCID 197562086-Methyl-7-(alpha,alpha,alpha-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.08 g. of 3-aminopyrazole-4-carbonitrile, 25 ml. of glacial acetic acid and 2.57 g. of 3-dimethylamino-2-methyl-3'-(trifluoromethyl)acrylophenone is refluxed for 8 hours and then evaporated to a crystalline solid. A methylene chloride solution of this solid is treated as described in Example 1, giving the desired product, m.p. 191°-193° C.

Workup

  1. additionA mixture of 1.08 g
  2. customevaporated to a crystalline solid
  3. additionA methylene chloride solution of this solid is treated

Sources & evidence

ORD record
ord-d36622dee21345ab96123d5fa9233aea
Source dataset
uspto-grants-1979_12
Patent number
US04178449

Linked notes

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