Ammonium Chloride → Methyl-[5-(4-chlorophenyl)-3-methyl-1-(pyrimidin-5-yl)-1h-pyrazol-4-yl]acetate

HRID 2068476Notes

Reaction equation

[F-].[Cs+].CC(C)([O-])C.[K+].[CH3:9][O:10][C:11](=[O:26])[CH2:12][C:13]1[C:14]([CH3:25])=[N:15][NH:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1.[N:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[N:29][CH:28]=1.[Cl-].[NH4+]>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:9][O:10][C:11](=[O:26])[CH2:12][C:13]1[C:14]([CH3:25])=[N:15][N:16]([C:31]2[CH:32]=[N:27][CH:28]=[N:29][CH:30]=2)[C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 20 °C

Procedure

0.287 g (2 mmol) of cesium fluoride, 0.103 g (1 mmol) of copper(II) acetate and 0.212 g (2 mmol) of potassium tert-butoxide 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. 0.234 g (2 mmol) of 5-pyrimidinylboronic acid was then added, and the mixture was stirred at 20° C. for 45 h. The mixture was then added to saturated ammonium chloride solution (10 ml) 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 0.040 g of product (5.8% of theory).

Workup

extractionextracted with dichloromethane
dry with materialThe combined organic phases were dried with magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-e5415bb0317048769b49d3787c39ea4c
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08298994B2

Reaction notes

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