Boron Trichloride → HCID 178436789, compound

Participants

Reaction Steps

BCl3 (1 M in CH2Cl2, 2.5 mL, 2.5 mmol, 5 eq) was added to a stirred solution of N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynyl-6-methyl pyrimidin-2-yl)thiophene-2-sulfonamide (230 mg, 0.50 mmol, 1.0 eq) in CH2Cl2 (10 mL) at rt 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/isopropanol to afford the title compound 5-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-5-ethynyl-6-methylpyrimidin-2-yl)thiophene-2-sulfonamide (Compound 267) (175.0 mg, 87.5%). LC-MS (m/z)=401.1 [M+H]+. δ (400 MHz, DMSO-d6): 0.81-0.85 (m, 2H), 1.03-1.07 (m, 2H), 1.99-2.04 (m, 1H), 2.55 (s, 3H), 5.17 (s, 1H), 6.49 (s, 1H), 7.61 (d, J=3.6 Hz, 1H), 7.88 (s, 2H), 7.91 (d, J=3.6 Hz, 1H), 9.21 (s, 1H)

Provenance & Evidence