Triethylamine → 4-(2,2-Dimethyl-propylamino)-5-[3-oxo-3-(4-[1,2,3]triazol-1-yl-phenyl)-prop-1-ynyl]-pyrimidine-2-carbonitrile

HRID 1984243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984243
[N:1]1([C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[N:2]1.C(Cl)(=O)C(Cl)=O.[CH3:21][C:22]([CH3:36])([CH3:35])[CH2:23][NH:24][C:25]1[C:30]([C:31]#[CH:32])=[CH:29][N:28]=[C:27]([C:33]#[N:34])[N:26]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C.[Cu]I.CCOC(C)=O.CCCCCC>[CH3:21][C:22]([CH3:36])([CH3:35])[CH2:23][NH:24][C:25]1[C:30]([C:31]#[C:32][C:10](=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([N:1]3[CH:5]=[CH:4][N:3]=[N:2]3)=[CH:14][CH:13]=2)=[CH:29][N:28]=[C:27]([C:33]#[N:34])[N:26]=1

Komponenten

10

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 226280454-(1H-1,2,3-triazol-1-yl)benzoic acidHCID 577141354-(2,2-Dimethyl-propylamino)-5-ethynyl-pyrimidine-2-carbonitrile

Produkt 1

HCID 577141314-(2,2-Dimethyl-propylamino)-5-[3-oxo-3-(4-[1,2,3]triazol-1-yl-phenyl)-prop-1-ynyl]-pyrimidine-2-carbonitrileAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 6228DimethylformamideKatalysatorHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-[1,2,3]Triazol-1-yl-benzoic acid (5.0 mmol) is dissolved in CH2Cl2 (20 ml). Oxalyl chloride (3.5 mmol) and DMF (1 drop) are added at room temperature and the reaction mixture is stirred at room temperature for 3 h, then evaporated. The residue is dissolved in CH2C2 (20 ml) and the mixture is added to 4-(2,2-dimethyl-propylamino)-5-ethynyl-pyrimidine-2-carbonitrile, copper (I) iodide (0.13 mmol) and triethylamine (13.0 mmol) at room temperature. The reaction mixture is stirred for overnight at room temperature. The organic layer is washed with brine, dried over magnesium sulfate and concentrated. The crude product is purified by silica gel column chromatography to give the product in 31% yield. Rf=0.02 (n-hexane:AcOEt=2:1)

Aufarbeitung

  1. customevaporated
  2. dissolutionThe residue is dissolved in CH2C2 (20 ml)
  3. stirringThe reaction mixture is stirred for overnight at room temperature
  4. washThe organic layer is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product is purified by silica gel column chromatography
  8. customto give the product in 31% yield

Quellen und Nachweise

ORD-Eintrag
ord-60f639cdeaae4888a3bb5ee33124be62
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544688B2

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