Allyl bromide → Ethyl 6-(allyloxy)-5-(benzyloxy)-2-(methylthio)pyrimidine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methylsulfanyl-1,6-dihydro-6-oxo-5-(phenylmethoxy)-4-pyrimidinecarboxylic acid, ethyl ester (4.28 g, 13.36 mmol) in DMF (70 mL) was added Cs2CO3 (4.35 g, 13.36 mmol) followed by 3-bromoprop-1-ene (1.156 mL, 13.36 mmol). The resulting mixture was stirred at 80° C. for 1 h, cooled to room temperature and partitioned between ethyl acetate and hexane. The organic phase was washed with water followed by brine, dried (Na2SO4) and filtered. Concentration gave an oil that was purified by flash column chromatography (Biotage flash chromatography system, 0%-40% ethyl acetate/hexane, 16 CV) to give the title compound as a yellow oil (1.8144 g, 38% yield). 1H NMR (300 MHz, CDCl3) δ: 7.41-7.37 (2H, m), 7.36-7.28 (3H, m), 6.10-5.97 (1H, m), 5.40 (2H, dq, J=17.2, 1.5 Hz), 5.29 (2H, dq, J=10.5, 1.2 Hz), 5.03 (2H, s), 4.93 (2H, dt, J=5.6, 1.4 Hz), 4.32 (2H, q, J=7.1 Hz), 4.32 (2H, q, J=7.1 Hz), 2.50 (2H, q, J=7.1 Hz), 1.28 (3H, t, J=7.1 Hz). LCMS (M+H) calcd for C18H21N2O4S: 361.12; found: 361.21.

Provenance & Evidence