Tributyltin Chloride → 4-Methyl-2-(4-tributylstannanyl-imidazol-1-yl)-6-(4-trifluoromethyl-phenyl)-pyrimidine

HRID 1989249Notes

Reaction equation

HRID 1989249 reaction equation
I[C:2]1[N:3]=[CH:4][N:5]([C:7]2[N:12]=[C:11]([CH3:13])[CH:10]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[N:8]=2)[CH:6]=1.[Cl-].[Li+].C([Mg]Cl)(C)C.[CH2:31]([Sn:35](Cl)([CH2:40][CH2:41][CH2:42][CH3:43])[CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH3:34].[Cl-].[NH4+]>C1COCC1>[CH3:13][C:11]1[CH:10]=[C:9]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[N:8]=[C:7]([N:5]2[CH:6]=[C:2]([Sn:35]([CH2:36][CH2:37][CH2:38][CH3:39])([CH2:40][CH2:41][CH2:42][CH3:43])[CH2:31][CH2:32][CH2:33][CH3:34])[N:3]=[CH:4]2)[N:12]=1

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 574687852-(4-Iodo-imidazol-1-yl)-4-methyl-6-(4-trifluoromethyl-phenyl)-pyrimidineHCID 178461733HCID 178461733, compound

Product 1

HCID 574688294-Methyl-2-(4-tributylstannanyl-imidazol-1-yl)-6-(4-trifluoromethyl-phenyl)-pyrimidineYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-(4-iodo-imidazol-1-yl)-4-methyl-6-(4-trifluoromethyl-phenyl)-pyrimidine (Example E.71) (0.43 g, 1.0 mmol) in THF (7 mL) was added at 0° C. iso-propylmagnesium 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, 93%) as a light yellow oil. MS (ISP) 595.3 [(M+H)+].

Workup

  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)

Sources & evidence

ORD record
ord-81466201deb24eda8a95f735126e1b31
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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