Compound 11
7-Bromo-3-((4-hydroxypiperidin-4-yl)methyl)thieno[3,2-d]pyrimidin-4(3H)-one
From: Discovery and characterization of highly potent and selective allosteric USP7 inhibitors
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
A solution of tert-butyl 4-((7-bromo-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl)methyl)-4-hydroxypiperidine-1-carboxylate 10 (250 mg, 0.563 mmol) was stirred in DCM (3 mL) and TFA (3 mL) for 20 min before the reaction was purified using a 10 g SCX-2 cartridge (10% MeOH in DCM then 20% 7 M NH3 in MeOH in DCM) to give the title compound (189 mg, 98%) as a colourless solid. LCMS: RT = 0.36 min, m/z = 344, 346 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 8.30 (s, 1H), 7.78 (s, 1H), 4.11 (s, 2H), 2.95 – 2.85 (m, 4H), 1.70 – 1.58 (m, 2H), 1.56 – 1.46 (m, 2H). 13C NMR (101 MHz, CDCl3): δ 158.07, 154.07, 150.04, 131.75, 123.03, 109.35, 70.63, 55.50, 42.03, 36.30.
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348266813
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