Boron Trichloride → (Z)-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(prop-1-enyl)pyrimidin-2-yl)thiophene-2-sulfonamide

Participants

Reaction Steps

BCl3 (1 M in CH2Cl2, 3.28 mL, 3.28 mmol, 4.0 equiv.) was added to a stirred solution of (Z)—N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(prop-1-enyl)pyrimidin-2-yl)thiophene-2-sulfonamide (375.6 mg, 0.82 mmol, 1.0 equiv.) in CH2Cl2 (20 mL) at room temperature under nitrogen. The reaction mixture was stirred for 30 min and then quenched with aq. NaHCO3 in ice bath. The reaction mixture was extracted with ethyl acetate and washed with water, brine, dried and evaporated. The crude product was crystallized with THF/isopropyl to afford (Z)-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(prop-1-enyl)pyrimidin-2-yl)thiophene-2-sulfonamide (Compound 207) (255.1 mg, 77.4%). LC-MS (m/z)=403 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.75-0.76 (m, 2H), 0.95-1.00 (m, 2H), 1.79-1.81 (m, 2H), 1.90 (d, J=6.0 Hz, 1H), 1.93-1.97 (m, 1H), 5.60-6.04 (m, 0.6H), 6.26-6.31 (m, 0.4H), 6.46-6.49 (s, 1.5H), 6.79 (d, J=15.2 Hz, 0.4H), 7.57-7.59 (m, 1H), 7.74-7.79 (m, 3H), 8.19 (s, 0.6H), 8.39 (s, 0.4H), 8.94 (s, 0.5H), 9.33 (s, 0.3H).

Provenance & Evidence