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

温度

0 °C

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)+].

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)

ORDレコード

ord-33b52e64007241fc9e95cc873c0681bc

出典データセット

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07642264B2