反应详情

To a solution of 4-Methyl-2-(methylthio)pyrimidine (1) (3 g, 21.40 mmol) in THF (35.7 mL) at −10° C. was added LHMDS (32.1 mL, 32.1 mmol, 1M in THF). The resulting reaction was warmed to rt and stirred for 15 minutes, after which time the reaction was cooled back to −10° C. and Benzyl Acetate (3.21 mL, 23.54 mmol) was added. The reaction was then warmed to rt and stirred for 1 hour, after which time complete conversion to product was observed by LCMS. TLC after 1 hour still showed the presence of some starting material and the reaction was continued stirring for an additional hour. After this time there was no change in TLC and the reaction was worked up. The reaction was quenched by slow addition of saturated ammonium chloride and the volatile solvent evaporated. The mixture was then diluted with EtOAc and water. The organic layer was then washed with brine, dried with sodium sulfate, and concentrated. The crude residue was purified by flash chromatography with a gradient of 8-66% EtOAc in Heptane to give the desired product as a yellow liquid (1.93 g, 50%). MS (ES+): m/z=183.1 (100) [MH+]. HPLC: tR=0.91 minute over 3 minutes. Purity: 76% [HPLC (LC/MS) at 220 nm].

1. customThe resulting reaction
2. temperatureafter which time the reaction was cooled back to −10° C.
3. temperatureThe reaction was then warmed to rt
4. stirringstirred for 1 hour
5. waitTLC after 1 hour still showed
6. stirringthe presence of some starting material and the reaction was continued stirring for an additional hour
7. customThe reaction was quenched by slow addition of saturated ammonium chloride
8. customthe volatile solvent evaporated
9. additionThe mixture was then diluted with EtOAc and water
10. washThe organic layer was then washed with brine
11. dry with materialdried with sodium sulfate
12. concentrationconcentrated
13. customThe crude residue was purified by flash chromatography with a gradient of 8-66% EtOAc in Heptane