Water → 6-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-1H-pyrazin-2-one

HRID 2194403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194403
C([O:4][C:5]1[CH:10]=[N:9][CH:8]=[C:7]([N:11]2[CH:15]=[C:14]([C:16]#[C:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[N:13]=[C:12]2[CH3:25])[N:6]=1)C=C.C1([SiH3])C=CC=CC=1.O>C(Cl)Cl>[Cl:24][C:20]1[CH:19]=[C:18]([C:17]#[C:16][C:14]2[N:13]=[C:12]([CH3:25])[N:11]([C:7]3[NH:6][C:5](=[O:4])[CH:10]=[N:9][CH:8]=3)[CH:15]=2)[CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 12752PhenylsilaneHCID 668656112-Allyloxy-6-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-pyrazine

Produkt 1

HCID 668653666-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-1H-pyrazin-2-oneAusbeute 45,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 75 mg (0.214 mmol) 2-Allyloxy-6-[4-(3-chloro-phenylethynyl)-2-methyl imidazol-1-yl]-pyrazine in 5 ml of methylene chloride was degassed with argon. Then 0.052 ml (0.428 mmol) of phenyl silane and 2.5 mg (0.002 mmol) of tetrakis(triphenyl-phosphine)palladium were added and the mixture was stirred for 1 h at room temperature. Then water (1 ml) was added and the mixture was vigourously stirred for 5 min., diluted with 10 ml of methylene chloride and the organic phase was washed with water and brine, dried over magnesium sulfate and concentrated. The obtained solid was triturated with benzene to remove impurities (triphenylphosphine oxide), filtered and dried to yield 30 mg (0.097 mmol, 45%) of the title compound as a white crystalline solid, MS: m/e=311.1, 313.1 (M+H+)

Aufarbeitung

  1. stirringthe mixture was vigourously stirred for 5 min.
  2. washthe organic phase was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe obtained solid was triturated with benzene
  6. customto remove impurities (triphenylphosphine oxide)
  7. filtrationfiltered
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3d334f4b4c1f4ce09d63fa3ca7a79fdd
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334287B2

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