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

HRID 349224Notes

Reaction equation

HRID 349224 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[N:11]=[C:12]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[O:13][CH:14]=2)=[N:6][CH:7]=1.[CH2:27]([N:31]1[CH:35]=[CH:34][N:33]=[N:32]1)[CH2:28][C:29]#[CH:30].C(NC(C)C)(C)C.C(OCC)(=O)C>CN(C=O)C.C1COCC1.[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:31]1([CH2:27][CH2:28][C:29]#[C:30][C:2]2[CH:3]=[N:4][C:5]([O:8][CH2:9][C:10]3[N:11]=[C:12]([CH:15]=[CH:16][C:17]4[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=4)[O:13][CH:14]=3)=[N:6][CH:7]=2)[CH:35]=[CH:34][N:33]=[N:32]1

Participants

9

Reactant 4

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 184535221-But-3-ynyl-1H-[1,2,3]triazoleHCID 694890165-Bromo-2-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine

Product 1

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

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-2-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine (0.213 g, 0.50 mmol), 1-but-3-ynyl-1H-[1,2,3]triazole (0.067 g, 0.55 mmol) and diisopropyl amine (iPr2NH) (2 ml) in DMF (4 ml) and THF (2 ml), copper iodide (CuI) (0.0048 g, 0.025 mmol) is added under stirring. After passing a stream of argon through the mixture for 10 min tetrakis(triphenylphosphine)palladium (0.029 g, 0.025 mmol) is added and the mixture is heated at 80° C. for 3 h. Ethyl acetate (150 ml) is added, the resulting mixture is washed with ammonium chloride (NH4Cl) and brine, dried over MgSO4 and concentrated in vacuo. The crude product is purified by flash column chromatography (chloroform (100%)->ethyl acetate (100%)) yielding 5-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-2-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine as a pale yellow solid. Yield 138 mg (59%).

Workup

  1. customfor 10 min
  2. additionis added
  3. washthe resulting mixture is washed with ammonium chloride (NH4Cl) and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by flash column chromatography (chloroform (100%)->ethyl acetate (100%))

Sources & evidence

ORD record
ord-8c86f036660d403a8cf61ccb24dff528
Source dataset
uspto-grants-2007_02
Patent number
US07179812B2

Reaction notes

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