Reaction #73125

Reaction equation

(R)-2-(2-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

4-(methylsulfonyl)phenylboronic acid

sodium hydroxide

→

title compound

Yield 2.1%

(R)-8-cyclopentyl-7-ethyl-5-methyl-2-(2-(4-(methylsulfonyl)phenyl)-1H-imidazol-1-yl)-7,8-dihydropteridin-6(5H)-one

Yield 2.1%

Solvents

DME H2O

Conditions

Workup

1. 1
   Otherv/v) and a stream of nitrogen was bubbled through the mixture for 2 minutes
2. 2
   workup.ADDITIONThe reaction mixture was diluted with brine
3. 3
   Extractionextracted with EtOAc
4. 4
   Dryingdried with Na2SO4
5. 5
   Otherthen purified by silica gel column chromatography and preparative HPLC
6. 6
   Otherto give

Procedure

(R)-2-(2-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 65, 0.15 g, 0.37 mmol), 4-(methylsulfonyl)phenylboronic acid (0.148 g, 0.74 mmol), aqueous sodium hydroxide (240 μL of 3N) and Pd(PPh3)4 (42 mg, 0.037 mmol) were dissolved in 1.2 mL of DME/H2O (5/1, v/v) and a stream of nitrogen was bubbled through the mixture for 2 minutes. The resulting solution was stirred at 90° C. for 18 h. The reaction mixture was diluted with brine, extracted with EtOAc, dried with Na2SO4 then purified by silica gel column chromatography and preparative HPLC to give to give the title compound (3.8 mg). LCMS: 481.2 m/z (M+H)+; ret. Time: 6.19 min (Analytical Method C).

Source