反应详情

温度

-78 °C

An oven dried flask, equipped with stir bar and septa, was charged with 4-chloro-2-(methylthio)pyrimidine-5-carbonyl chloride (Aaron Chemistry, 1338 mg, 6 mmol). The flask was capped with septa, evacuated and backfilled with nitrogen (three times). The solid was dissolved in tetrahydrofuran (24.0 mL), cooled to −78° C. and kept under nitrogen. (2-Chlorobenzyl)magnesium chloride (14.40 mL, 7.20 mmol) was then slowly added. After the addition was completed, the dry ice/acetone bath was removed and the mixture was stirred at ambient temperature for 3 hours. The mixture was quenched with aqueous 1 M HCl (50 mL), extracted with ethyl acetate (3×80 mL) and the combined extracts were washed with brine, dried over magnesium sulfate (MgSO4), filtered and concentrated. The crude product obtained was purified by flash chromatography (Isco®, Redi-Sep® column, 0-30% ethyl acetate/hexane, linear gradient) to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 8.72 (s, 1H), 7.47-7.36 (m, 1H), 7.36-7.21 (m, 3H), 4.41 (s, 2H), 2.61 (s, 3H); MS (ESI) m/z 313 (M+H)+.

1. customAn oven dried flask
2. customequipped
3. customThe flask was capped with septa
4. customevacuated
5. dissolutionThe solid was dissolved in tetrahydrofuran (24.0 mL)
6. additionAfter the addition
7. customthe dry ice/acetone bath was removed
8. stirringthe mixture was stirred at ambient temperature for 3 hours
9. customThe mixture was quenched with aqueous 1 M HCl (50 mL)
10. extractionextracted with ethyl acetate (3×80 mL)
11. washthe combined extracts were washed with brine
12. dry with materialdried over magnesium sulfate (MgSO4)
13. filtrationfiltered
14. concentrationconcentrated
15. customThe crude product obtained
16. customwas purified by flash chromatography (Isco®, Redi-Sep® column, 0-30% ethyl acetate/hexane, linear gradient)