Sodium Hydroxide → 5-(1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)picolinic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)picolinate (130 mg, 0.24 mmol) in dioxane/H2O (8 mL/8 mL) was added NaOH (70 mg, 1.75 mmol), the reaction mixture was heated to 35° C. with stirring for 30 minutes, the dioxane was removed in vacuo, and the aqueous layer was adjusted to pH=4-5 with conc. HCl, the precipitate was collected by filtration and washed with methanol (5 mL) to afford 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)picolinic acid (98 mg, 76.2%) as an orange solid. 1H NMR (300 MHz, DMSO): δ 10.58 (s, 1H), 9.68 (s, 1H), 8.87 (s, 2H), 8.24 (dd, 1H, J1=8.7 Hz, J2=2.4 Hz), 8.03 (d, 1H, J=8.7 Hz), 7.67 (d, 1H, J=2.1 Hz), 7.35 (dd, 1H, J1=8.7 Hz, J2=2.1 Hz), 6.82 (brs, 1H), 4.84-4.65 (m, 2H), 3.77-3.65 (m, 6H), 3.18-3.00 (m, 2H), 2.67-2.64 (m, 1H), 2.05-1.75 (m, 4H). LC-MS: 536 [M+H]+, tR=1.50 min. HPLC: 97.47% at 214 nm, 97.48% at 254 nm, tR=4.096 min.

Provenance & Evidence