Реакция #162613
ord-4154d87023ea401f98c68234a7cdf863
Уравнение реакции
Реактанты
Реагенты
Растворители
Условия реакции
Обработка
- 1ДругоеIn a 250 mL round-bottomed flask was placed
- 2Другоеto give a suspension
- 3Другоеresulting in a yellow precipitate
- 4ТемператураThe mixture was slowly warmed to room temperature
- 5Другоеquenched with NaOH (5M) to pH˜8
- 6workup.ADDITIONAqueous sodium thiosulfate was added
- 7ЭкстракцияThe mixture was extracted with dichloromethane
- 8Сушкаdried over MgSO4
- 9Концентрированиеconcentrated
- 10workup.ADDITIONThe crude product was added to a silica gel column
- 11Промывкаwas eluted with ethyl acetate in hexanes (10-40%)
- 12КонцентрированиеCollected fractions were concentrated
Методика
In a 250 mL round-bottomed flask was placed 8-(2,6-dichloropyrimidin-4-yl)-3-oxa-8-azabicyclo[3.2.1]octane (34, 980 mg, 3.77 mmol) in chloroform (4 ml) to give a very light yellow solution. Sodium iodide (941 mg, 6.28 mmol) was added to give a suspension. The mixture was cooled to 0° C. and an aqueous solution (57% w/w) of hydrogen iodide (4.97 ml, 37.7 mmol) was added, resulting in a yellow precipitate. The mixture was slowly warmed to room temperature and stirred at room temperature for 4 h. The mixture was diluted with water and quenched with NaOH (5M) to pH˜8. Aqueous sodium thiosulfate was added to decolorize. The mixture was extracted with dichloromethane, dried over MgSO4 and concentrated. The crude product was added to a silica gel column and was eluted with ethyl acetate in hexanes (10-40%). Collected fractions were concentrated to give the title compound (516 mg) as a white solid. LCMS analysis revealed that the product contained ˜20% starting material. The mixture was used without further purification in the next step.