3-Carboxyphenylboronic acid → 3-{6-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-2-methylsulfanyl-pyrimidin-4-yl}-benzoic acid

Participants

Reaction Steps

By proceeding in a similar manner to Example 16(a) above but using commercially available 3-carboxy-phenyl-boronic acid, and (6-chloro-2-methylsulfanyl-pyrimidin-4-yl)-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine (0.57 g) in Step 2, and extracting the reaction mixture (adjusted to pH 2) with EtOAc followed by evaporation of the organic extract, there is prepared 3-{6-[2-(3,4-dimethoxy-phenyl)-ethylamino]-2-methylsulfanyl-pyrimidin-4-yl}-benzoic acid [0.48 g, Example 16(b)]. LCMS: RT=2.75 minutes, MS: 426 (M+H). IC50=243 nM

Provenance & Evidence