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

HRID 349232Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 349232
Br[C:2]1[CH:3]=[N:4][C:5]([Cl:8])=[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.ClCCl>CN(C=O)C.[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>[Cl:8][C:5]1[N:4]=[CH:3][C:2]([C:12]#[C:11][CH2:10][CH2:9][N:13]2[CH:17]=[CH:16][N:15]=[N:14]2)=[CH:7][N:6]=1

Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 184535221-But-3-ynyl-1H-[1,2,3]triazole

Produkt 1

HCID 860740652-Chloro-5-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Bromo-2-chloro-pyrimidine (0.500 g, 2.53 mmol), 1-but-3-ynyl-1H-[1,2,3]triazole (0.368 g, 3.03 mmol) and triethyl amine (NEt3) (5.0 ml) are dissolved in DMF (10 ml) and copper iodide (CuI) (0.052 g, 0.27 mmol) is added under stirring. After passing a stream of argon through the mixture for 10 min tetrakis(triphenylphosphine)palladium(0) (0.149 g, 0.13 mmol) is added and stirring is continued for 4 h at 80° C. Dichloromethane (125 ml) is added, the mixture is washed with 0.5N hydrochloric acid (HCl) and brine, dried over Na2SO4 and concentrated in vacuo. The crude product is purified by flash column chromatography (ethyl acetate/hexanes 4:1) yielding 2-chloro-5-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-pyrimidine as a colorless solid. Yield 373 mg (63%).

Aufarbeitung

  1. customfor 10 min
  2. additionis added
  3. stirringstirring
  4. washthe mixture is washed with 0.5N hydrochloric acid (HCl) and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by flash column chromatography (ethyl acetate/hexanes 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-f91b44a73c43430ca8b37cdd5930fb50
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179812B2

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