N2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-chloro-1,3-benzoxazol-2-amine → Rac-n2-(4-{4-amino-1-[1-(2-methoxyethyl)tetrahydro-1h-3-pyrrolyl]-1h-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5-chloro-1,3-benzoxazol-2-amine monoacetate

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rac-N2-(4-{4-Amino-1-[1-(2-methoxyethyl)tetrahydro-1H-3-pyrrolyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5-chloro-1,3-benzoxazol-2-amine monoacetate was prepared from rac-3-iodo-1-[1-(2-methoxyethyl)tetrahydro-1H-3-pyrrolyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.200 g, 0.319 mmol) and N2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-chloro-1,3-benzoxazol-2-amine (0.148 g, 0.399 mmol) in a manner similar to that used for the preparation of cis-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-fluorophenyl)-1,3-benzoxazol-2-amine. The compound was formed as an off-white solid (0.080 g, 50%). 1H NMR (DMSO-d6, 400 MHz) 1.91 (s, 3H), 2.33 (m, 2H), 2.66 (m, 2H), 2.75-2.85 (m, 3H), 3.17 (t, 1H), 3.24 (s, 3H), 3.45 (t, 2H), 5.37 (m, 1H), 7.18 (d, 1H), 7.55 (d, 2H), 7.68 (d, 2H), 7.92 (d, 2H), 8.24 (s, 1H), 9.80 (s, 1H); RP-HPLC Rt 11.337 min, 97% purity (5% to 85% acetonitrile/0.1M aqueous ammonium acetate, buffered to pH 4.5, over 20 min at 1 mL/min; λ=254 nm; Deltapak C18, 300 Å, 5 μm, 150×3.9 mm column); m/z 505 (MH+).

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