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

HRID 1242328Notes

Reaction equation

HRID 1242328 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH:8]([C:12]1[C:13]([CH:28]2[CH2:30][CH2:29]2)=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[N:16][CH:17]=1)[CH2:9][CH2:10][CH3:11].[C:31]([O:35][C:36](=[O:47])[CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([SH:45])=[CH:41][C:40]=1[CH3:46])([CH3:34])([CH3:33])[CH3:32]>CN(C=O)C.CCOCC>[C:31]([O:35][C:36](=[O:47])[CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([S:45][CH:8]([C:12]2[C:13]([CH:28]3[CH2:30][CH2:29]3)=[N:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)=[N:16][CH:17]=2)[CH2:9][CH2:10][CH3:11])=[CH:41][C:40]=1[CH3:46])([CH3:34])([CH3:33])[CH3:32]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 21935892[Rac]-5-(1-chloro-butyl)-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidineHCID 67072235(4-Mercapto-2-methyl-phenoxy)-acetic acid tert-butyl ester

Product 1

HCID 67072430[Rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-butylsulfanyl}-2-methyl-phenoxy)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

231 mg (0.7 mmol) cesium carbonate was added to a solution of 210 mg (0.59 mmol) [rac]-5-(1-chloro-butyl)-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine (example 30D]) and 151 mg (0.59 mmol) (4-mercapto-2-methyl-phenoxy)-acetic acid tert-butyl ester (example 28C]) in 3 ml DMF. After stirring for 3 h at RT, the reaction mixture was taken up in ether and washed with 1N HCl and water. The crude product was purified by chromatography over silica gel with AcOEt/heptane 1:9 providing 257 mg of pure [rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-butylsulfanyl}-2-methyl-phenoxy)-acetic acid tert-butyl ester.

Workup

  1. washwashed with 1N HCl and water
  2. customThe crude product was purified by chromatography over silica gel with AcOEt/heptane 1:9 providing 257 mg of pure [rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-butylsulfanyl}-2-methyl-phenoxy)-acetic acid tert-butyl ester

Sources & evidence

ORD record
ord-6a084f8d061746d5bca88df9a32ca2c6
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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