Sodium Hydroxide → 2-(5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophen-2-yl)-2-oxoacetic acid

Participants

Reaction Steps

To a solution of ethyl 2-(5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophen-2-yl)-2-oxoacetate (Compound 189) (50 mg, 0.12 mmol, 1.0 eq) in ethanol (15 mL) was added 1 N NaOH (0.5 mL, 0.48 mmol, 4.0 eq). The mixture was stirred at room temperature for 1 hour, then, concentrated and the residue was redissolved in water. To the solution was added 1N HCl (0.5 mL) and the mixture was stirred for 0.5 h at 23° C. The solution was filtered to afford 2-(5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophen-2-yl)-2-oxoacetic acid Compound 190) (30 mg, 64.3%). LC-MS (m/z): 390.0 [M+]+. 1H NMR (400 MHz, DMSO-d6): δ 0.74-0.78 (m, 2H), 0.96-1.01 (m, 2H), 1.92-1.96 (m, 1H), 6.42 (s, 1H), 7.87 (d, J=4.0 Hz, 1H), 8.07 (d, J=4.4 Hz, 1H), 8.49 (s, 1H), 9.51 (s, 1H), 13.28 (bs, 1H).

Provenance & Evidence