Ethyl Acetate → 2-(4-[1,2,3]Triazol-1-yl-butyl)-5-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine

HRID 349230Notes

Reaction equation

HRID 349230 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[O:6][CH:7]=1.[N:20]1([CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[N:34]=[CH:33][C:32]([OH:35])=[CH:31][N:30]=2)[CH:24]=[CH:23][N:22]=[N:21]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C=O)C>[N:20]1([CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[N:34]=[CH:33][C:32]([O:35][CH2:2][C:3]3[N:4]=[C:5]([CH:8]=[CH:9][C:10]4[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=4)[O:6][CH:7]=3)=[CH:31][N:30]=2)[CH:24]=[CH:23][N:22]=[N:21]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 690682904-Chloromethyl-2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazoleHCID 694861582-(4-[1,2,3]Triazol-1-yl-butyl)-pyrimidin-5-ol

Product 1

HCID 694862962-(4-[1,2,3]Triazol-1-yl-butyl)-5-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chlormethyl-2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazole (0.144 g, 0.50 mmol), 2-(4-[1,2,3]triazol-1-yl-butyl)-pyrimidin-5-ol (0.078 g, 0.357 mmol) and cesium carbonate (Cs2CO3) (0.175 g, 0.536 mmol) in DMF (10 ml) is kept at 80° C. for 2 h. After cooling ethyl acetate (25 ml) is added, the mixture is washed with sat. NH4Cl and brine, dried over MgSO4 and concentrated in vacuo. The crude product is purified by flash column chromatography (ethyl acetate (100%)->ethyl acetate/methanol 9:1) and 2-(4-[1,2,3]-triazol-1-yl-butyl)-5-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine can be isolated as a white solid. Yield 40 mg (24%).

Workup

  1. additionis added
  2. washthe mixture is washed with sat. NH4Cl and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by flash column chromatography (ethyl acetate (100%)->ethyl acetate/methanol 9:1) and 2-(4-[1,2,3]-triazol-1-yl-butyl)-5-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine
  6. customcan be isolated as a white solid

Sources & evidence

ORD record
ord-01b6a3316a4b48c09b545a12f8434f42
Source dataset
uspto-grants-2007_02
Patent number
US07179812B2

Reaction notes

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