Sodium Hydroxide → HCID 66549518, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)picolinate (80 mg, 0.15 mmol) in dioxane/H2O (60 mL/6 mL) was added NaOH (60 mg, 1.5 mol), the reaction mixture was heated to 35° C. with stirring for 1 hour, then 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 water (5 mL) and dried to afford 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)picolinic acid as brown solid (67 mg, 84.8%). 1H NMR (300 MHz, DMSO): δ 9.56 (s, 1H), 9.06 (s, 1H), 8.96 (d, 1H, J=6.3 Hz), 8.79 (s, 1H), 8.33 (dd, 1H, J1=8.1 Hz, J2=1.8 Hz), 8.07 (d, 1H, J=8.1 Hz), 7.86 (s, 1H), 7.50 (brs, 1H), 6.90 (d, 1H, J=8.7 Hz), 4.60-4.58 (brs, 1H), 3.76-3.52 (m, 10H), 2.30-2.24 (m, 1H), 2.11-2.07 (m, 1H). LC-MS: 522 [M+H]+, tR=1.31 min. HPLC: 98.03% at 214 nm, 97.82% at 254 nm, tR=3.20 min.

Provenance & Evidence