反应详情

温度

-10 °C

iPrMgCl (2M in THF, 1.1 mL) was added dropwise to a solution of methyl thieno[2,3-d]pyrimidine-6-carboxylate (intermediate 11) (138 mg) and N-methoxy-N-methylamide (104 mg) in THF at −20° C. maintaining the internal temperature below −5° C. The reaction was allowed to stir at −10° C. for 30 minutes and then quenched with NH4Cl (sat. aq). The solution was diluted with EtOAc and the organic layer was separated. The aqueous layer was extracted with EtOAc (2×15 mL) and then the combined organics dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with hexane:EtOAc (1:1 to 1:4) afforded the title compound as a pale yellow solid (107 mg, 67%);

1. temperaturemaintaining the internal temperature below −5° C
2. customquenched with NH4Cl (sat. aq)
3. additionThe solution was diluted with EtOAc
4. customthe organic layer was separated
5. extractionThe aqueous layer was extracted with EtOAc (2×15 mL)
6. dry with materialthe combined organics dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customPurification by flash chromatography on silica eluting with hexane:EtOAc (1:1 to 1:4)