تفاعل #162651
ord-a6b6069accb04e3389fe6ce281a0e9e2
معادلة التفاعل
المتفاعلات
المذيبات
ظروف التفاعل
المعالجة
- 1أخرىto give a yellow biphasic solution
- 2أخرىThe solution was degassed with nitrogen for 10 minutes
- 3أخرىThe vial was sealed
- 4درجة الحرارةthe reaction was heated to 120° C. for an additional 80 minutes under microwave irradiation
- 5درجة الحرارةThe vessel was then cooled to room temperature
- 6ترشيحthe reaction mixture was filtered through Celite™
- 7غسيلThe filter cake was washed with ethyl acetate
- 8تركيزthe filtrate was then concentrated under reduced pressure
- 9أخرىto provide a brown oil
- 10غسيلwas eluted with 0-10% methanol in methylene chloride
الإجراء التجريبي
A microwave vial was charged with 1-(6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-2-chloropyrimidin-4-yl)-N,N-dimethylmethanamine (0.400 g, 1.42 mmol) and sodium carbonate (2M in water, 2.12 mL, 4.24 mmol). DME (7 mL) was then added to give a yellow biphasic solution. The solution was degassed with nitrogen for 10 minutes, and tetrakis(triphenylphosphine)palladium(0) (0.098 g, 0.085 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.372 g, 1.697 mmol) were added. The vial was sealed and heated to 120° C. for 40 minutes under microwave irradiation. LCMS indicated that the reaction had not gone to completion. Additional tetrakis(triphenylphosphine)palladium(0) (0.049 g, 0.043 mmol) was added and the reaction was heated to 120° C. for an additional 80 minutes under microwave irradiation. The vessel was then cooled to room temperature and the reaction mixture was filtered through Celite™. The filter cake was washed with ethyl acetate and the filtrate was then concentrated under reduced pressure to provide a brown oil. The crude product was added to a silica gel column and was eluted with 0-10% methanol in methylene chloride to provide 4-(4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-((dimethylamino)methyl)pyrimidin-2-yl)aniline (0.365 g, 76%) as a light orange solid. HRMS; [M+H]+ Obs'd=340.2133, [M+H]+ Calc'd=340.2131