1,3-Butanedione, 1-(4-chloro-3-methylphenyl)-4,4,4-trifluoro- → 5-(4-Chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

HRID 269000Notes

Reaction equation

HRID 269000 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=O)[C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[CH3:17].[NH2:18][C:19]1[CH:23]=[CH:22][NH:21][N:20]=1>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[N:20]3[N:21]=[CH:22][CH:23]=[C:19]3[N:18]=2)=[CH:4][C:3]=1[CH3:17]

Participants

4

Reactant 2

HCID 670009781,3-Butanedione, 1-(4-chloro-3-methylphenyl)-4,4,4-trifluoro-HCID 178418806HCID 178418806, compound

Product 1

HCID 670002385-(4-Chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidineYield 98.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(4-chloro-3-methyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione (3.95 g, 14.9 mmol) and commercially available 3-aminopyrazole (1.24 g, 14.9 mmol) in acetic acid (40 mL) was refluxed for 5.5 h and evaporated. The crude product was further purified by crystallization (ethyl acetate/hexane) to yield 5-(4-chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine (4.57 g, 98%) as a yellow solid. MS (EI) 311.2 [(M)+]; mp 114° C.

Workup

  1. temperaturewas refluxed for 5.5 h
  2. customevaporated
  3. customThe crude product was further purified by crystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-64932a50cc344d23a02d47bdaf83aac5
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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