Triethylamine → HCID 73446456, Verbindung

HRID 1271040

Reaktionsgleichung

Reaktionsgleichung von HRID 1271040
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:17][C:18]1[C:23](I)=[CH:22][N:21]=[C:20]([N:25]=[CH:26][N:27]([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])[N:19]=1>C(#N)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:23]2[C:18]([Cl:17])=[N:19][C:20]([N:25]=[CH:26][N:27]([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:29])[CH3:30])=[N:21][CH:22]=2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 136603Benzene, 1-bromo-4-ethynyl-HCID 734464514-Chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine

Produkt 1

HCID 73446456HCID 73446456, VerbindungAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 0.5 g of 1-bromo-4-ethynylbenzene, 5.0 mL of triethylamine, 0.031 mg of copper iodide, 0.94 g of 4-chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine and 0.046 g of dichlorobis(triphenyl)phosphine palladium II was magnetically stirred at room temperature for 18 hrs. The mixture was diluted with acetonitrile, filtered and the filtrate evaporated in vacuo. The evaporated filtrate was dissolved in dichloromethane and loaded on a column of silica gel equilibrated in the same solvent. Cuts were monitored by thin layer chromatography. After initial cuts of brown colored eluates, the product subsequently eluted as yellow fractions. Like cuts were pooled and evaporated to give 0.84 g of 5-(4-bromophenylethynyl)-4-chloro-2-diisopropylaminomethyleneaminopyrimidine as a thick amber syrup.

Aufarbeitung

  1. filtrationfiltered
  2. customthe filtrate evaporated in vacuo
  3. dissolutionThe evaporated filtrate was dissolved in dichloromethane
  4. washAfter initial cuts of brown colored eluates, the product subsequently eluted as yellow fractions
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6ec0d97fa2584cd3b1674bb15858e107
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205297B2

Verknüpfte Notizen

Wird geladen…