Cesium carbonate → HCID 67072237, compound

HRID 1242463Notes

Reaction equation

HRID 1242463 reaction equation
[CH2:1]([C:5]1[C:10]([CH2:11]Cl)=[CH:9][N:8]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].[CH2:23]([O:25][C:26](=[O:38])[C:27]([O:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1)([CH3:29])[CH3:28])[CH3:24].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOCC>[CH2:23]([O:25][C:26](=[O:38])[C:27]([O:30][C:31]1[CH:32]=[CH:33][C:34]([O:37][CH2:11][C:10]2[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][C:7]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)=[N:8][CH:9]=2)=[CH:35][CH:36]=1)([CH3:29])[CH3:28])[CH3:24]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 181741Ethyl 2-(4-hydroxyphenoxy)-2-methylpropanoateHCID 21935930HCID 21935930, compound

Product 1

HCID 67072237HCID 67072237, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 367 mg (1.11 mmol) 4-butyl-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidine (example 115C]) and 250 mg (1.11 mmol) 2-(4-hydroxy-phenoxy)-2-methyl-propionic acid ethyl ester [Newman, Melvin S.; Cella, James A. Monoalkylation of hydroquinone. Journal of Organic Chemistry (1974), 39(2), p 214–15] in 4 ml DMF was treated with 436 mg (1.34 mmol) cesium carbonate. The reaction mixture was stirred for 24 h at RT and then it 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 1:4 to provide 344 mg pure 2-{4-[4-butyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-phenoxy}-2-methyl-propionic acid ethyl ester.

Workup

  1. washwashed with 1N HCl and water
  2. customThe crude product was purified by chromatography over silica gel with AcOEt/heptane 1:4

Sources & evidence

ORD record
ord-dc41f0372dce4891a708ee433903f1c7
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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