Hydrochloric Acid → HCID 86651550, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophen-2-yl)methylcarbamate (Compound 168) (100 mg, 0.23 mmol, 1.0 equiv.) in EtOH (3 mL) was added HCl(g)/EtOH (saturated, 3 mL). After stirred at 20° C. for 12 h, the reaction mixture was concentrated in vacuum. The crude product was crystallized with THF/isopropyl to afford 2-(5-(aminomethyl)thiophen-2-yl)-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-ethynylpyrimidin-4-amine hydrochloride (Compound 167) (41.4 mg, 20.9%, two steps). LC-MS (m/z)=337.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.80-0.84 (m, 2H), 1.00-1.05 (m, 2H), 2.01-2.04 (m, 1H), 4.28 (d, J=5.2 Hz, 2H), 4.92 (s, 1H), 6.52 (s, 1H), 7.38 (d, J=3.6 Hz, 1H), 7.87 (d, J=4.0 Hz, 1H), 8.53 (s, 1H), 8.65 (bs, 2H), 9.13 (s, 1H).

Provenance & Evidence