Cesium carbonate → HCID 67072194, compound

HRID 1242432Notes

Reaction equation

HRID 1242432 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH2:19][CH2:20][O:21][CH3:22])=[N:5][C:6]([C:9]2[CH:10]=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=2)=[N:7][CH:8]=1.[CH2:23]([O:25][C:26](=[O:39])[C:27]([O:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][C:32]=1[CH3:38])([CH3:29])[CH3:28])[CH3:24].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:23]([O:25][C:26](=[O:39])[C:27]([O:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:2][C:3]2[C:4]([CH2:19][CH2:20][O:21][CH3:22])=[N:5][C:6]([C:9]3[CH:10]=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=3)=[N:7][CH:8]=2)=[CH:33][C:32]=1[CH3:38])([CH3:28])[CH3:29])[CH3:24]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoateHCID 21935855HCID 21935855, compound

Product 1

HCID 67072194HCID 67072194, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 133 mg (0.40 mmol) 5-chloromethyl-4-(2-methoxy-ethyl)-2-(6-trifluoromethyl-pyridin-3-yl)-pyrimidine (example 101F]) and 95 mg (0.40 mmol) 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590) in 12 ml of acetonitrile was added 143 mg (0.44 mmol) cesium carbonate. The reaction mixture was stirred for 16 h at RT. The mixture was filtered, taken up in dichloromethane dried (Na2SO4) and evaporated. The crude product was purified by flash chromatography over silica gel with heptane/AcOEt 9:1, to give 119 mg of the title compound as light yellow viscous oil.

Workup

  1. filtrationThe mixture was filtered
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe crude product was purified by flash chromatography over silica gel with heptane/AcOEt 9:1

Sources & evidence

ORD record
ord-69788a65c4454fd2b916f8f5ae1c788b
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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