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

HRID 349226ノート

反応式

HRID 349226 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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%))

出典と根拠

ORDレコード
ord-3d6e179fd1804e4eb8db8408c6db88e2
出典データセット
uspto-grants-2007_02
特許番号
US07179812B2

反応ノート

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