Sodium Hydroxide → 4-[1-(2-aminopyrimidin-4-yl)-3-methyl-1H-indazol-6-yl]-2-hydroxy-2-methylbut-3-ynoic acid

Participants

Reaction Steps

To a solution of ethyl 4-[1-(2-aminopyrimidin-4-yl)-3-methyl-1H-indazol-6-yl]-2-hydroxy-2-methylbut-3-ynoate (120 mg, 0.33 mmol) in methanol (0.5 mL) was introduced sodium hydroxide (0.16 mL of a 2M aqueous solution, 0.33 mmol). After 15 hr at RT, the reaction mixture was concentrated in vacuo and the pH of the aqueous residue adjusted to 7 with 0.5M aqueous hydrochloric acid. The solution was extracted with 3:1 chloroform/isopropanol (5×5 mL extractions) and the combined organic extracts dried (Na2SO4), filtered and concentrated in vacuo to furnish the crude title compound as a yellow solid: 1H NMR (250 MHz, DMSO) delta 1.68 (3H, s), 2.59 (3H, s), 7.07-7.29 (3H, m), 7.37 (2H, dd, J=8.4, 1.2 Hz), 7.87 (1H, d, J=7.7 Hz), 8.28 (1H, d, J=5.9 Hz), 8.85 (1H, s); LC-MS: m/z=+338.00 (M+H)+. This compound, with LC-MS purity=100% UV, was used in the next step without further purification.

Provenance & Evidence