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 (1.92 g, 6.52 mmol) in tetrahydrofuran (50 mL) and treat with N-methylmorpholine (0.77 mL, 6.52 mmol). Cool to -20° C. and treat with isobutyl chloroformate (0.86 mL, 6.52 mmol). Stir for 1 hour and add a solution of 1,3-dipropyl-5,6-diaminouracil (1.48 g, 6.52 mmol) in dimethylformamide (4 mL). Stir at -20° C. for 3 hours and warm to room temperature. Stir for 2 hours and dilute with chloroform (400 mL). Separate the organic phase and wash with saturated sodium hydrogen carbonate (300 mL), then brine (2×400 mL). Dry (Na2SO4) and evaporate the solvent in vacuo to give 4.31 g crude product. Purify by flash chromatography (10→15→20% isopropanol/hexane) to give the title compound (2.16 g, 66%); [α]d 20 =-45.8 ° (C=1.00, CHCl3).

Provenance & Evidence