Diisobutylaluminumhydride → 6-bromo-3-(3-hydroxypropyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-(6-bromo-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propanoate (5.1 g, 14.96 mmol) in THF (500 mL) at −60° C., was added diisobutylaluminium hydride (1.5 M in toluene, 40 mL, 60 mmol) dropwise. The reaction was stirred at −60° C. for 3 h, warmed to 0° C., quenched with aq. NH4Cl (150 mL) then extracted with EA (200 mL). The organic layer was washed with brine (100 mL), dried over Na2SO4 and concentrated to give 6-bromo-3-(3-hydroxypropyl)-1-methylpyrido[2,3-d]pyrimidine-2,4 (1H,3H)-dione (6.2 g, >100% yield) as a yellow oil. LCMS: MH+ 314 and TR=0.882 min. Used without further purification.

Provenance & Evidence