Formic Acid → 3-(5-benzyl-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydro pyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(3-(tert-butyldimethylsilyloxy)propyl)-5-(hydroxy(phenyl)methyl)-1-methyl-6-(3-(trifluoromethoxy)phenyl)pyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione (100 mg, 0.162 mmol) in HCOOH (2 mL) was added Zn dust (105 mg, 1.62 mmol). The reaction was heated at 40° C. for 6 h, cooled to RT then diluted with EA (5 mL) and water (1 mL). The organic layer was washed with brine (1 mL), dried over Na2SO4, and concentrated to a residue which was purified by Prep TLC eluted with PE/EA (2:1) to give 3-(5-benzyl-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydropyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate, LCMS: MH+ 514 and TR=1.790 min and 3-(5-benzyl-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2,7,8-tetrahydropyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate, LCMS: MH+ 516 and TR=1.714 min, (66.7 mg, 80% yield) as an oil. Used without further purification.

Provenance & Evidence