Water → N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(hydroxymethyl)pyrimidin-2-yl)thiophene-2-sulfonamide

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Reaction Steps

A solution of N-tert-butyl-5-(5-((tert-butyldimethylsilyloxy)methyl)-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide (120 mg, 0.24 mmol, 1.0 equiv.) and TBAF (0.3 ml, 0.29 mmol, 1.2 equiv.) in THF (5 mL) was stirred for 0.5 h at 23° C. Water was added and the reaction was extracted with EtOAc (3×50 ml). The combined organic phases were washed (brine), dried (Na2SO4), filtered and concentrated to afford N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(hydroxymethyl)pyrimidin-2-yl) thiophene-2-sulfonamide (Compound 163) (89.0 g, 86.34%) as white solid. LC-MS (m/z)=449.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ 0.75 (m, 2H), 0.96-0.98 (m, 2H), 1.20 (s, 9H), 1.93 (m, 1H), 4.56 (d, 4.4 Hz, 2H), 5.62 (s, 1H), 6.52 (s, 1H), 7.59 (d, J=3.6 Hz, 1H), 7.76 (d, J=3.6 Hz, 1H), 7.86 (s, 1H), 8.23 (s, 1H), 8.96 (s, 1H), 12.18 (s, 1H)

Provenance & Evidence