1-Chloro-4-(chloromethyl)benzene → HCID 118871741, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 3-(1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (See Intermediate 1, 60 mg, 0.141 mmol) in DMF (2 mL) was added 1-chloro-4-(chloromethyl)benzene (45.4 mg, 0.282 mmol), followed by K2CO3 (58.5 mg, 0.423 mmol). The reaction was heated at 85° C. for 18 h, cooled to RT then diluted with EA (10 mL) and brine (5 mL). The organic layer was washed with aq. 1N LiCl (3×20 mL), dried over Na2SO4 and concentrated to a residue which was purified by chromatography PE/EA (5:1 to 2:1) to give 3-(5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (30 mg, 38.7% yield) as a solid. LCMS: MH+ 550 and TR=2.078 min.

Provenance & Evidence