1,2-Dimethoxyethane → 4-(2-chloropyrimidin-4-yl)-N,N-dimethylaniline

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-dimethylaminophenyl boronic acid (10 g, 60.6 mM), 2,4-dichloropyrimidine (9 g, 60.4 mM), Na2CO3 (12 g, 114.2 mM), tetrakistriphenylphosphine palladium (2.5 g, 2.1 mM), dimethoxyethane (120 ml) and water (35 ml) was heated at 80° C. under a nitrogen atmosphere for 16 hr. The reaction was cooled in an ice bath and the resulting yellow suspension was filtered and the solid washed with water (3×50 ml) then ethyl acetate (2×50 ml). The solid was dried in vaccuo to afford [4-(2-Chloro-pyrimidin-4-yl)-phenyl]-dimethyl-amine (11.1 g, 78% yield) as an orange solid. ES-MS MH+234, 236, 1H NMR (300 MHz, ppm, DMSO-d6): 8.57 (d, 1H), 8.05 (d, 2H), 7.92 (d, 1H), 6.80 (d, 1H), 3.03 (s, 6H)

Provenance & Evidence