5-Decyloxy-2-(4-bromophenyl)pyrimidine → (-)-5-Decyloxy-2-[4-(6-hydroxyheptynyl)phenyl]pyrimidine

Participants

Reaction Conditions

Reaction Steps

In a reactor equipped with a stirrer and a thermometer, 5-decyloxy-2-(4-bromophenyl)pyrimidine (25 g), optically active 6-hydroxy-1-heptyne (8.58 g), dichlorobis(triphenylphosphine)palladium (0.1 g), copper iodide (0.1 g), triphenylphosphine (0.52 g) and triethylamine (200 ml) are charged and heated up to 90° C. to carry out a reaction for 10 hours. After evaporating triethylamine off under reduced pressure, toluene and 10% hydrochloric acid are added to the residue for extraction, and the organic layer is washed with water and evaporated under reduced pressure. A resulting residue is purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain (-)-5-decyloxy-2-[4-(6-hydroxyheptynyl)phenyl]-pyrimidine (23.4 g). [α]D20 =-3.3° (c=1.035, CHCl3).

Provenance & Evidence