4-Methylmorpholine → Tert-butyl 2-[4-[3-[(4-amino-2,6-dioxo-1,3-dipropylpyrimidin-5-yl)amino]-2-methyl-3-oxopropyl]phenoxy]acetate

Participants

Reaction Conditions

Reaction Steps

Dissolve (+)-4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid (3.02 g, 10.27 mmol) in tetrahydrofuran (100 mL) and treat with N-methylmorpholine (1.2 mL, 10.27 mmol). Cool to -20° C., add isobutyl chloroformate (1.35 mL, 10.27 mmol) and stir for 1 hour. Add a solution of 1,3-dipropyl-5,6-diaminouracil (2.33 g, 10.27 mmol) in dimethylformamide (8 mL) and stir for 6 hours at -20° C. Warm to room temperature and dilute with chloroform (600 mL). Wash with saturated sodium hydrogen carbonate (300 mL), then brine (3×300 mL). Dry (MgSO4) and evaporate the solvent in vacuo. Purify by flash chromatography (5→10→15→20% isopropanyl/hexane) to give the title compound as a foam (3.74 g, 72%); [α]d 20 =+51.4° (C=1.03, CHCl3).

Provenance & Evidence