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

HRID 349226노트

반응식

HRID 349226 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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%))

출처 및 근거

ORD 기록
ord-3d6e179fd1804e4eb8db8408c6db88e2
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179812B2

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