HCID 86606993, compound → HCID 57982521, compound

HRID 1868445Notes

Reaction equation

HRID 1868445 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:17]=[C:13]2[N:12]=[C:11]([CH3:24])[C:10]=1[C:25]([O-:27])=[O:26]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:17]=[C:13]2[N:12]=[C:11]([CH3:24])[C:10]=1[C:25]([OH:27])=[O:26]

Participants

4

Reactant 1

HCID 86606993HCID 86606993, compound

Product 1

HCID 57982521HCID 57982521, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 7-(2,4-dichlorophenyl)-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidine-6-carboxylate (27.5 mg, 0.07 mmol) in THF (2 mL) and H2O (0.5 mL) was added LiOHH2O (4.2 mg, 0.1 mmol). After 5 h at 50° C., the reaction was concentrated under reduced pressure and diluted with EtOAc (10 mL). The organic layer was extracted with 1N HCl (6 mL), saturated NH4Cl (10 mL) and brine, dried (MgSO4), filtered and concentrated. The crude reaction product, 7-(2,4-dichlorophenyl)-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid, was moved onto next step without further purification (purity ˜90%).

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. additiondiluted with EtOAc (10 mL)
  3. extractionThe organic layer was extracted with 1N HCl (6 mL), saturated NH4Cl (10 mL) and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude reaction product, 7-(2,4-dichlorophenyl)-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid
  8. customwas moved onto next step without further purification (purity ˜90%)

Sources & evidence

ORD record
ord-0a206d7c4d5e41e89cc98ef177660d3f
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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