Tributyltin Chloride → HCID 57468828, Verbindung

HRID 1927971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1927971
[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](I)[N:18]=[CH:17]3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl-].[Li+].C([Mg]Cl)(C)C.[CH2:29]([Sn:33](Cl)([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH3:32].[Cl-].[NH4+]>C1COCC1>[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:33]([CH2:34][CH2:35][CH2:36][CH3:37])([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:29][CH2:30][CH2:31][CH3:32])[N:18]=[CH:17]3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

6

Edukt 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 574687894-(3,4-Dichloro-phenyl)-2-(4-iodo-imidazol-1-yl)-6-methyl-pyrimidineHCID 178461733HCID 178461733, Verbindung

Produkt 1

HCID 57468828HCID 57468828, VerbindungAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 4-(3,4-dichloro-phenyl)-2-(4-iodo-imidazol-1-yl)-6-methyl-pyrimidine (Example E.75) (0.43 g, 1.0 mmol) in THF (7 mL) was added at 0° C. isopropyl-magnesium chloride lithium chloride (1M in THF, 1.22 mL, 1.22 mmol). The reaction mixture was allowed to stir for 15 min at 0° C., tributyltin chloride (0.43 g, 1.33 mmol) was added, the reaction mixture was stirred at room temperature for 5 h, poured into saturated ammonium chloride solution (30 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (30 mL), dried (MgSO4) and evaporated. The crude product was further purified by flash chromatography on silica gel (ethylacetate/heptane) to yield the title compound (0.55 g, 92%) as a light yellow oil. MS (ISP) 593.2 [(M+H)+].

Aufarbeitung

  1. customwas added at 0° C.
  2. stirringthe reaction mixture was stirred at room temperature for 5 h
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layers were washed with brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was further purified by flash chromatography on silica gel (ethylacetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-b7a45e59174d473f89af514593f01aab
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183262B2

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