Chloroform → 5-Bromo-2-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-pyrimidine

HRID 349226Notes

Reaction equation

HRID 349226 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[CH2:9]([N:13]1[CH:17]=[CH:16][N:15]=[N:14]1)[CH2:10][C:11]#[CH:12].C(N(CC)CC)C.C(Cl)(Cl)Cl>CN(C=O)C.[Cu](I)I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:12]#[C:11][CH2:10][CH2:9][N:13]2[CH:17]=[CH:16][N:15]=[N:14]2)=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 70066515-Bromo-2-iodopyrimidineHCID 184535221-But-3-ynyl-1H-[1,2,3]triazole

Product 1

HCID 691357895-Bromo-2-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-pyrimidine

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

5-Bromo-2-iodo-pyrimidine (1.14 g, 4.0 mmol), 1-but-3-ynyl-1H-[1,2,3]triazole (0.533 g, 4.4 mmol) and triethyl amine (NEt3) (2 ml) are dissolved in DMF (1 ml) and copper iodide (CuI) (0.38 g, 0.2 mmol) is added under stirring. After passing a stream of argon through the mixture for 10 min bis(triphenylphosphine) palladium(II) dichloride (0.140 g, 0.2 mmol) is added and stirring is continued for 3 h at r.t. Chloroform (300 ml) is added; the mixture is washed with 1N HCl and water, dried over MgSO4 and concentrated in vacuo. The residue is purified by flash column chromatography (chloroform (100%)->ethyl acetate (100%)) yielding 5-bromo-2-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-pyrimidine as a beige solid. Yield 0.96 g (86%).

Workup

  1. customfor 10 min
  2. additionis added
  3. stirringstirring
  4. washthe mixture is washed with 1N HCl and water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash column chromatography (chloroform (100%)->ethyl acetate (100%))

Sources & evidence

ORD record
ord-3d6e179fd1804e4eb8db8408c6db88e2
Source dataset
uspto-grants-2007_02
Patent number
US07179812B2

Reaction notes

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