1-Ethyl-4-ethynylbenzene → 4-Chloro-2-diisopropylaminomethyleneamino-5-(4-ethylphenylethynyl)pyrimidine

HRID 1271039

Reaktionsgleichung

Reaktionsgleichung von HRID 1271039
[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.[CH2:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]#[CH:27])=[CH:22][CH:21]=1)[CH3:19]>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.[Cu](I)I.C(N(CC)CC)C>[Cl:1][C:2]1[C:7]([C:19]#[C:18][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH3:27])=[CH:22][CH:21]=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 1424251-Ethyl-4-ethynylbenzeneHCID 734464514-Chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine

Produkt 1

HCID 734464504-Chloro-2-diisopropylaminomethyleneamino-5-(4-ethylphenylethynyl)pyrimidineAusbeute 63,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 6.3 g of 4-chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine, 33 mL of triethylamine, 2.43 g of 4-ethyl-1-ethynylbenzene, 0.304 g of dichlorobis(triphenyl)phosphine palladium II and 0.21 g copper iodide was magnetically stirred at reflux temperature for 1.5 hrs. The mixture was filtered and the filtrate evaporated in vacuo. Both the precipitate and the evaporated filtrate were dissolved in dichloromethane and washed with water, dried over sodium sulfate, filtered and evaporated. The residues were dissolved in 1:1 dichloromethane-hexanes and separately purified by column chromatography. After initial elution with 1:1 dichloromethane-hexanes, the product was obtained by elution with dichloromethane and 50% ethyl acetate-dichloromethane. Evaporation of the eluates gave 4.04 g of 4-chloro-2-diisopropylaminomethyleneamino-5-(4-ethylphenylethynyl)pyrimidine as a thick amber syrup.

Aufarbeitung

  1. temperatureat reflux temperature for 1.5 hrs
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated in vacuo
  4. dissolutionBoth the precipitate and the evaporated filtrate were dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. dissolutionThe residues were dissolved in 1:1 dichloromethane-hexanes
  10. customseparately purified by column chromatography
  11. washAfter initial elution with 1:1 dichloromethane-hexanes
  12. customthe product was obtained by elution with dichloromethane and 50% ethyl acetate-dichloromethane
  13. customEvaporation of the eluates

Quellen und Nachweise

ORD-Eintrag
ord-00d218d8dd114839b00fe84d3161ce11
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205297B2

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