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

HRID 349225Notes

Reaction equation

HRID 349225 reaction equation
[N:1]1([CH2:6][CH2:7][C:8]#[C:9][C:10]2[CH:11]=[N:12][C:13]([O:16][CH2:17][C:18]3[N:19]=[C:20]([CH:23]=[CH:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)[O:21][CH:22]=3)=[N:14][CH:15]=2)[CH:5]=[CH:4][N:3]=[N:2]1>C(OCC)(=O)C.[Pd]>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:11]=[N:12][C:13]([O:16][CH2:17][C:18]3[N:19]=[C:20]([CH:23]=[CH:24][C:25]4[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:29][CH:30]=4)[O:21][CH:22]=3)=[N:14][CH:15]=2)[CH:5]=[CH:4][N:3]=[N:2]1

Participants

4

Reactant 1

HCID 694883845-(4-[1,2,3]Triazol-1-yl-but-1-ynyl)-2-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine

Product 1

HCID 694866995-(4-Triazol-1-yl-butyl)-2-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-(4-[1,2,3]Triazol-1-yl-but-1-ynyl)-2-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine (0.047 g, 0.1 mmol) is dissolved in ethyl acetate (3 ml) and hydrogenated for 1 h at r.t. in the presence of palladium on charcoal (10%, 20 mg). After filtration and concentration in vacuo the crude product is purified by flash column chromatography (ethyl acetate/hexanes 1:3->ethyl acetate (100%)) yielding 5-(4-[1,2,3]-triazol-1-yl-butyl)-2-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine as a white solid. Yield 35 mg (74%)

Workup

  1. filtrationAfter filtration and concentration in vacuo the crude product
  2. customis purified by flash column chromatography (ethyl acetate/hexanes 1:3->ethyl acetate (100%))

Sources & evidence

ORD record
ord-aa495e9bfb42457a928102b53ab07bfa
Source dataset
uspto-grants-2007_02
Patent number
US07179812B2

Reaction notes

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