Heptane → 4-(3,4-Dichloro-phenyl)-2-[4-(3-methanesulfonyl-phenyl)-imidazol-1-yl]-6-methyl-pyrimidine

HRID 1928237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1928237
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([N:16]3[CH:20]=[C:19]([Sn](CCCC)(CCCC)CCCC)[N:18]=[CH:17]3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].BrC1C=C([CH2:41][S:42](CC2C=CC=C(Br)C=2)(=[O:44])=[O:43])C=CC=1.C[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([N:16]3[CH:20]=[C:19]([C:55]4[CH:56]=[CH:57][CH:58]=[C:59]([S:42]([CH3:41])(=[O:44])=[O:43])[CH:54]=4)[N:18]=[CH:17]3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

5

Edukt 3

HCID 8900HeptaneHCID 534433923-Bromophenylmethyl sulphoneHCID 57468828HCID 57468828, Verbindung

Produkt 1

HCID 574689844-(3,4-Dichloro-phenyl)-2-[4-(3-methanesulfonyl-phenyl)-imidazol-1-yl]-6-methyl-pyrimidineAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A stirred mixture of 4-(3,4-dichloro-phenyl)-6-methyl-2-(4-tributylstannanyl-imidazol-1-yl)-pyrimidine (Example G.4) (0.45 g, 0.76 mmol), commercially available 3-bromo-phenylmethyl sulfone (0.20 g, 0.83 mmol), tetrakis(triphenyl-phosphine)palladium (0.053 g, 0.046 mmol) in toluene (8 mL) was heated under reflux conditions for 15 h. Heptane (10 mL) was added at room temperature and the mixture was stirred for 1 h. The precipitate was collected by filtration, washed with heptane and dried to yield the title compound (0.27 g, 78%) as an off-white solid. MS (ISP) 459.2 [(M+H)+]; mp 213° C.

Aufarbeitung

  1. temperaturewas heated under reflux conditions for 15 h
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with heptane
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-841a0647ca684bf5941138d75787c718
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183262B2

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