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

Temperature

0 °C

To a stirred solution of 4-(4-chloro-phenyl)-2-(4-iodo-imidazol-1-yl)-6-trifluoromethyl-pyrimidine (Example E.70) (0.45 g, 1.0 mmol) in THF (5 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 16 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 (0.29 g, 47%) as a light yellow oil. MS (ISP) 615.3 [(M+H)+].

1. customwas added at 0° C.
2. stirringthe reaction mixture was stirred at room temperature for 16 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)

ORD record

ord-745eee4d7524412eb92327a7ed7c6d9b

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07642264B2