Tributyltin Chloride → 4-(4-Chloro-3-methyl-phenyl)-6-methyl-2-(4-tributylstannanyl-imidazol-1-yl)-pyrimidine

HRID 1927975Notes

Reaction equation

HRID 1927975 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]3[CH:19]=[C:18](I)[N:17]=[CH:16]3)[N:9]=2)=[CH:4][C:3]=1[CH3:21].[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:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]3[CH:19]=[C:18]([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:17]=[CH:16]3)[N:9]=2)=[CH:4][C:3]=1[CH3:21]

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 574687904-(4-Chloro-3-methyl-phenyl)-2-(4-iodo-imidazol-1-yl)-6-methyl-pyrimidineHCID 178461733HCID 178461733, compound

Product 1

HCID 574688324-(4-Chloro-3-methyl-phenyl)-6-methyl-2-(4-tributylstannanyl-imidazol-1-yl)-pyrimidineYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-(4-chloro-3-methyl-phenyl)-2-(4-iodo-imidazol-1-yl)-6-methyl-pyrimidine (Example E.76) (1.03 g, 2.51 mmol) in THF (20 mL) was added at 0° C. isopropyl-magnesium chloride lithium chloride (1M in THF, 3.05 mL, 3.05 mmol). The reaction mixture was allowed to stir for 15 min at 0° C., tributyltin chloride (1.14 g, 3.5 mmol) was added, the reaction mixture was stirred at room temperature for 15 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 alox (ethylacetate/heptane) to yield the title compound (1.19 g, 83%) as a yellow oil. MS (ISP) 575.3 [(M+H)+].

Workup

  1. customwas added at 0° C.
  2. stirringthe reaction mixture was stirred at room temperature for 15 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 alox (ethylacetate/heptane)

Sources & evidence

ORD record
ord-d8c121e5285f470b9dfeebb67b1bfd99
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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