Reaction #47851

Reaction equation

1,4-dioxane

N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

cesium fluoride

6-bromo-2-(2-morpholinoethyl)thieno[2,3-d]pyrimidine

→

title compound

N-Cyclopropyl-4-methyl-3-(2-(2-morpholinoethyl)thieno[2,3-d]pyrimidin-6-yl)benzamide

Solvents

EtOAc

water

Conditions

Workup

1. 1
   Filtrationfiltered through Celite®
2. 2
   OtherThe organic solutions were evaporated under reduced pressure
3. 3
   Washwashed with saturated sodium bicarbonate (1×25 mL)
4. 4
   Dryingdried over MgSO4
5. 5
   OtherThe organic solutions were evaporated under reduced pressure
6. 6
   Otherchromatographed through a Redi-Sep pre-packed silica gel column (40 g)
7. 7
   Washeluting with a gradient of 5% to 95% MeOH in DCM

Procedure

A 5 ml glass microwave reaction vessel was charged with 6-bromo-2-(2-morpholinoethyl)thieno[2,3-d]pyrimidine. (0.200 g, 0.582 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.135 g, 0.582 mmol), cesium fluoride (0.277 g, 1.75 mmol), tetrakis(triphenylphosphine)palladium(0) (0.046 g, 0.040 mmol), 1,4-dioxane (1 mL, 57 mmol) and water (1 ml). The reaction mixture was heated in a Smith Synthesizer microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 150° C. for 20 min. The reaction mixture was diluted with EtOAc and filtered through Celite®. The organic solutions were evaporated under reduced pressure. The crude residue was suspended in DCM and washed with saturated sodium bicarbonate (1×25 mL) followed by brine (1×25 mL), water (1×25 mL) and dried over MgSO4. The organic solutions were evaporated under reduced pressure and the residue was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 5% to 95% MeOH in DCM to provide the title compound (0.095 g) MS (ES+): 438 (M+H)+.

Source