Bromobenzene → 3-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-1-phenyldihydropyrimidine-2,4(1H,3H)-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-dihydropyrimidine-2,4(1H,3H)-dione (100 mg, 0.35 mmol), from this Example step 1, bromobenzene (0.037 mL, 0.35 mmol), tris(dibenzylideneacetone)dipalladium (6.4 mg, 0.01 mmol), Xanthphos (0.0121 g, 0.021 mmol) and Cs2CO3 (0.171 g, 0.52 mmol) were combined in dry dioxane (1 mL) and stirred at 100° C. overnight in a sealed tube. The reaction mixture was partitioned between ethyl acetate and water. Combined organic extracts were washed with water and brine, dried over Na2SO4 and the solvent evaporated in vacuo. The product was purified by preparative TLC using ethyl acetate and hexane (30:70) to give the title compound.

Provenance & Evidence