Hydrochloric Acid → (E)-6-amino-2-(4-chloro-2,3-difluorophenyl)-5-(2-(trimethylsilyl)vinyl)pyrimidine-4-carboxylic acid

Participants

Reaction Steps

A 2M solution of aqueous sodium hydroxide (400 μL, 0.80 mmol, 2.0 equiv) was added to a stirred suspension of (E)-methyl 6-amino-2-(4-chloro-2,3-difluorophenyl)-5-(2-(trimethylsilyl)vinyl)pyrimidine-4-carboxylate (160 mg, 0.40 mmol, 1.0 equiv) in methanol (4.0 mL) at 23° C. The resulting heterogeneous yellow mixture was stirred at room temperature for 3 h. The reaction mixture was adjusted to approximately pH 4 via dropwise addition of concentrated hydrochloric acid and concentrated under vacuum. The residue was slurried in water and vacuum filtered to afford the title compound as an off-white powder (130 mg, 87%): mp 155-157° C.; 1H NMR (300 MHz, (CD3)2SO) δ 7.77 (m, 1H), 7.51 (m, 1H), 7.31 (br s, 2H); 6.77 (d, J=19 Hz, 1H), 6.30 (d, J=19 Hz, 1H), 0.12 (s, 9H); IR (neat) 3514 (s), 3475 (s), 3407 (s), 3336 (s), 3218 (m), 2963 (m), 1768 (m), 1640 (m), 1612 (m); ESIMS m/z 384 ([M+H]+).

Provenance & Evidence