8-Cyclopentyltheophylline → 7-(2-Chloro-6-fluorobenzyl)-8-cyclopentyl-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione

Participants

Reaction Conditions

Reaction Steps

A solution of 8-cyclopentyl-1,3-dimethylxanthine (100 mg, 0.40 mmol) and K2CO3 (80 mg, 0.58 mmol) was treated with 2-chloro-6-fluorobenzyl bromide (142 mg, 0.64 mmol) dissolved in 400 μL DMF. The reaction mixture was sealed and heated to 60° C. for 24 hrs. The reaction mixture was cooled and purified by preparative thin layer chromatography (silica gel, 1 mm plate, EM Science 20×20 cm silica gel 60 F264) eluting with EtOAc:hexane (1:1) to give 23 mg (14% yield) of the title compound as a white solid: 1H NMR (CDCl3, 400 MHz) 7.29-7.11 (m, 2H), 7.01-6.85 (m, 1H), 5.86 (s, 2H), 3.54 (s, 3H), 3.38 (s, 3H); 3.02-2.81 (m, 1H), 1.83-1.43 (m, 8H); MS (ESP+) m/e 391 (MH+); TLC(EtOAc:hexanes/1:1) Rf=0.58.

Provenance & Evidence