Water → HCID 58169183, compound

Participants

Reaction Steps

A solution of 3-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophen-2-yl)-3-hydroxypropyl acetate C-243 (390 mg, 0.92 mmol, 1.0 equiv.) in MeOH (10 mL) was stirred at 23° C., 1 NNaOH was added until the PH of the solution reached 11˜12. After 1 hour, H2O (20 mL) and 1 NHCl were added until the PH of the solution reached 3-4. The reaction mixture was extracted with THF and washed with water, brine, dried and evaporated. The crude product was crystallized with THF/isopropyl to afford 1-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophen-2-yl)propane-1,3-diol (Compound 242) (250 mg, 71.3%). LC-MS (m/z)=382.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.75 (m, 2H), 0.98-1.00 (m, 2H), 1.84-1.88 (m, 2H), 1.93-1.98 (m, 1H), 3.47-3.59 (m, 2H), 4.53 (t, J=4.8 Hz, 1H), 4.84 (s, 1H), 4.92-4.96 (m, 1H), 5.72 (d, J=4.8 Hz, 1H), 6.54 (s, 1H), 7.02 (d, J=3.6 Hz, 1H), 7.72 (d, J=3.2 Hz, 1H), 8.45 (s, 1H), 8.55 (s, 1H), 12.27 (s, 1H).

Provenance & Evidence