Cesium carbonate → [Rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethylsulfanyl}-2-methyl-phenoxy)-acetic acid tert-butyl ester

HRID 1242321Notes

Reaction equation

HRID 1242321 reaction equation
Cl[CH:2]([C:4]1[C:5]([CH:20]2[CH2:22][CH2:21]2)=[N:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:8][CH:9]=1)[CH3:3].[C:23]([O:27][C:28](=[O:39])[CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([SH:37])=[CH:33][C:32]=1[CH3:38])([CH3:26])([CH3:25])[CH3:24].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:23]([O:27][C:28](=[O:39])[CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([S:37][CH:2]([C:4]2[C:5]([CH:20]3[CH2:22][CH2:21]3)=[N:6][C:7]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=3)=[N:8][CH:9]=2)[CH3:3])=[CH:33][C:32]=1[CH3:38])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 21935642[Rac]-5-(1-chloro-ethyl)-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidineHCID 67072235(4-Mercapto-2-methyl-phenoxy)-acetic acid tert-butyl ester

Product 1

HCID 67072435[Rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethylsulfanyl}-2-methyl-phenoxy)-acetic acid tert-butyl esterYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 180 mg (0.551 mmol) [rac]-5-(1-chloro-ethyl)-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine (example 28H]) and 140 mg (0.551 mmol) (4-mercapto-2-methyl-phenoxy)-acetic acid tert-butyl ester in 3 ml DMF was added 315 mg (0.66 mmol) cesium carbonate. The reaction mixture was stirred for 3 h at RT and then partitioned between ether, 1N HCl and water. The crude product was purified by chromatography over silica gel with AcOEt/Heptan 1:9 to give 150 mg of pure [rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethylsulfanyl}-2-methyl-phenoxy)-acetic acid tert-butyl ester.

Workup

  1. custompartitioned between ether, 1N HCl and water
  2. customThe crude product was purified by chromatography over silica gel with AcOEt/Heptan 1:9

Sources & evidence

ORD record
ord-7f8d2ca5e8f64315a73d480fb321aca9
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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