反应详情

Sodium thiomethoxide (140 mg, 2 mmol) was added to 4-chloro-2-methyl-6-(tributylstannyl)pyrimidine (835 mg, 2 mmol) in tetrahydrofuran (10 mL). The reaction mixture was stirred at room temperature for 48 h. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (5 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as an orange oil. The crude product was purified by silica gel chromatography, eluting with 5% EtOAc/hexanes to give 2-methyl-4-(methylthio)-6-(tributylstannyl)pyrimidine (256 mg, 30% yield). 1H NMR (300 MHz, CDCl3) δ 7.07 (s, 1H); 2.62 (s, 3H); 2.51 (s, 3H); 1.44-1.70 (m, 6H); 1.21-1.42 (m, 6H); 0.98-1.21 (m, 6H); 0.91 (t, 9H).

1. extractionextracted with EtOAc (2×30 mL)
2. extractionThe organic extract
3. washwas washed with saturated NaCl (5 mL)
4. dry with materialdried over Na2SO4
5. filtrationThe solution was filtered
6. concentrationconcentrated in vacuo
7. customto give the crude material as an orange oil
8. customThe crude product was purified by silica gel chromatography
9. washeluting with 5% EtOAc/hexanes