Hydrochloric Acid → (E)-6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-(2-(trihydroxysilyl)vinyl)pyrimidine-4-carboxylic acid

Participants

Reaction Steps

A 2M aqueous solution of sodium hydroxide (150 μL, 0.31 mmol, 1.05 equiv) was added to a stirred solution of (E)-methyl 6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-(2-(triethoxysilyl)vinyl)pyrimidine-4-carboxylate (145 mg, 0.29 mmol, 1.0 equiv) in 3:1 methanol:tetrahydrofuran (4.0 mL) at room temperature. The homogeneous yellow solution was stirred at room temperature for 20 h. The reaction mixture was adjusted to pH 4 using concentrated hydrochloric acid and concentrated under vacuum. The residue was slurried in water and vacuum filtered to provide the title compound as a tan powder (95 mg, 81% yield): mp 220-250° C. (decomposition); IR (thin film) 3323 (m), 3195 (m), 2944 (w), 1603 (s), 1534 (s) cm−1; 1H NMR (400 MHz, DMSO-d6) δ 7.56-7.76 (m, 1H), 6.59-7.52 (m, 4H), 3.93 (br s, 3H); ESIMS m/z 402 [(M+H)+].

Provenance & Evidence