Water → 3-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(hydroxymethyl)pyrimidin-2-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-tert-butyl-3-(5-((tert-butyldimethylsilyloxy)methyl)-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)benzenesulfonamide (400 mg, 0.718 mmol), BCl3/CH2Cl2 (10 mL, 10 mmol, 13.9 eq, 1 M) in CH2Cl2 (10 mL) was stirred at 20° C. under a nitrogen atmosphere for 30 h. Water (50 mL) was added into the mixture. The mixture was extracted with EtOAc (3×50 mL). The combined organic phases were washed (sat NaHCO3, brine), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel chromatography (CH2Cl2/MeOH 500:1 to 15:1 as eluent) to afford compound 3-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(hydroxymethyl)pyrimidin-2-yl)benzenesulfonamide (Compound 124) (28 mg, 10%) as yellowish solid. LC-MS (m/z)=387.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.81-0.82 (m, 2H), 0.94-0.98 (m, 2H), 1.92-1.95 (m, 1H), 4.61 (d, J=5.2 Hz, 2H), 5.65 (t, J=5.2 Hz, 1H), 6.54 (s, 1H), 7.44 (s, 2H), 7.72 (t, J=8 Hz, 1H), 7.95 (d, J=7.6 Hz, 1H), 8.35 (d, J=5.6 Hz, 1H), 8.51 (d, J=7.6 Hz, 1H), 8.84 (s, 1H), 8.92 (s, 1H), 12.18 (s, 1H).

Provenance & Evidence