Hydrochloric Acid → Methyl-[5-(4-chlorophenyl)-1-(2-chloropyrimidin-5-yl)-3-methyl-1h-pyrazol-4-yl]acetate

HRID 2068477Notes

Reaction equation

HRID 2068477 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][C:9](=[O:24])[CH2:10][C:11]1[C:12]([CH3:23])=[N:13][NH:14][C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1.[Cl:25][C:26]1[N:31]=[CH:30][C:29](B(O)O)=[CH:28][N:27]=1.Cl>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:7][O:8][C:9](=[O:24])[CH2:10][C:11]1[C:12]([CH3:23])=[N:13][N:14]([C:29]2[CH:28]=[N:27][C:26]([Cl:25])=[N:31][CH:30]=2)[C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 21747362(2-Chloropyrimidin-5-yl)boronic acidHCID 178499523HCID 178499523, compound

Product 1

HCID 131730040Methyl-[5-(4-chlorophenyl)-1-(2-chloropyrimidin-5-yl)-3-methyl-1h-pyrazol-4-yl]acetate

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

0.515 g (3 mmol) of copper(II) acetate and 0.306 ml (4 mmol) of pyridine were added to 0.5 g (2 mmol) of methyl[5-(4-chlorophenyl)-3-methyl-1H-pyrazol-4-yl]acetate in 10 ml of dichloromethane. 0.598 g (4 mmol) of 2-chloropyrimidine-5-boronic acid was then added, and the mixture was stirred at 20° C. for 24 h. The mixture was then added to 1 M HCl and extracted with dichloromethane. The combined organic phases were dried with magnesium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC. This gave 0.015 g of product (2% of theory).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic phases were dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-4ed2d21a9a9a4924bbec920782b89eb6
Source dataset
uspto-grants-2012_10
Patent number
US08298994B2

Reaction notes

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