Phenylacetylene → 4-Chloro-2-diisopropylaminomethyleneamino-5-phenylethynylpyrimidine

HRID 1271030

Reaktionsgleichung

Reaktionsgleichung von HRID 1271030
[Cl:1][C:2]1[C:7](I)=[CH:6][N:5]=[C:4]([N:9]=[CH:10][N:11]([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[N:3]=1.[C:18]1([C:24]#[CH:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[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.C(N(CC)CC)C>[Cl:1][C:2]1[C:7]([C:25]#[C:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:6][N:5]=[C:4]([N:9]=[CH:10][N:11]([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[N:3]=1

Komponenten

6

Edukt 2

HCID 10821PhenylacetyleneHCID 734464514-Chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine

Produkt 1

HCID 734464524-Chloro-2-diisopropylaminomethyleneamino-5-phenylethynylpyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 2.46 g 4-chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine, 7.5 mL triethylamine, 0.064 g copper iodide, 0.12 g dichlorobis(triphenyl)phosphine palladium II and 0.9 mL phenylacetylene was stirred under nitrogen at room temperature for two days. The dark brown mixture was evaporated in vacuo at a bath temperature of 30–35° C. The residue was partitioned between dichloromethane and water. The organic phase was washed thrice with water, dried over sodium sulfate, filtered and evaporated to yield 3.37 g of a dark brown oil. The residue was dissolved in hexanes and purified by column chromatography on silica gel, eluting successively with hexanes, 1:1 dichloromethane/hexanes and dichloromethane. The product was obtained from the latter eluant to yield after evaporation, 1.69 (74%) g of 4-chloro-2-diisopropylaminomethyleneamino-5-phenylethynylpyrimidine.

Aufarbeitung

  1. customThe dark brown mixture was evaporated in vacuo at a bath temperature of 30–35° C
  2. customThe residue was partitioned between dichloromethane and water
  3. washThe organic phase was washed thrice with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ac778f941d194820b478c15d66105573
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205297B2

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