HCID 86608002, compound → HCID 67000680, compound

HRID 269008Notes

Reaction equation

HRID 269008 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=O)[CH:11]([F:13])[F:12])=[CH:4][C:3]=1[CH3:16].[NH2:17][C:18]1[CH:22]=[CH:21][NH:20][N:19]=1>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:11]([F:13])[F:12])[N:19]3[N:20]=[CH:21][CH:22]=[C:18]3[N:17]=2)=[CH:4][C:3]=1[CH3:16]

Participants

4

Reactant 2

HCID 86608002HCID 86608002, compoundHCID 178418806HCID 178418806, compound

Product 1

HCID 67000680HCID 67000680, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(4-chloro-3-methyl-phenyl)-4,4-difluoro-butane-1,3-dione (7.18 g, 29.1 mmol) and commercially available 3-aminopyrazole (2.42 g, 29.1 mmol) in acetic acid (70 mL) was refluxed for 4.5 h and evaporated. The crude product was further purified by crystallization (ethyl acetate/hexane) to yield 5-(4-chloro-3-methyl-phenyl)-7-difluoromethyl-pyrazolo[1,5-a]pyrimidine (5.33 g, 62%) as an off-white solid. MS (EI) 293.2 [(M)+]; mp 107° C.

Workup

  1. temperaturewas refluxed for 4.5 h
  2. customevaporated
  3. customThe crude product was further purified by crystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f5887ffcb1c94f62b31ca5ab95e4734e
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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