Reaction #2031017

Reaction equation

8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

sodium bicarbonate

1-bromo-4-fluorobutane

→

title compound

Yield 60.1%

8-chloro-3-(4-fluorobutyl)-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

Yield 60.1%

Solvents

DMSO

methanol

Conditions

Workup

1. 1
   OtherThe vial was sealed
2. 2
   Temperatureheated
3. 3
   Otherpurified by mass

Procedure

To a solution of 8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (200 mg, 0.88 mmol, 1 eq) in anhydrous DMSO (1 ml) in a 1.5 ml microwave vial equipped with a stirrer was added sodium bicarbonate (113 mg, 1.07 mmol, 1.2 eq) followed by 1-bromo-4-fluorobutane (114 ul, 165 mg, 1.06 mmol, 1.2 eq). The vial was sealed and heated with stirring using a microwave, maintaining the temperature at 120° C. for 25 min with a maximum power output of 300 W. The resulting dark brown solution was diluted with methanol (1 ml) and purified by mass directed autopreparative HPLC to give the title compound as a white solid (159 mg, 60%). m/z 301.3[MH+]

Source