(R)-3-Pyrrolidinol → n2-(4-{4-Amino-1-[(3s)-1-(2-methoxyethyl)tetrahydro-1h-3-pyrrolyl]-1h-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5,7-dimethyl-1,3-benzoxazol-2-amine monoacetate

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N2-(4-{4-Amino-1-[(3S)-1-(2-methoxyethyl)tetrahydro-1H-3-pyrrolyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5,7-dimethyl-1,3-benzoxazol-2-amine monoacetate was prepared from (R)-(+)-3-pyrrolidinol in a manner analogous to that used for the preparation of rac-N2-(4-{4-amino-1-[1-(2-methoxyethyl)tetrahydro-1H-3-pyrrolyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5,7-dimethyl-1,3-benzoxazol-2-amine. The compound was formed as a pink solid (0.103 g, 53%). 1H NMR (DMSO-d6, 400 MHz) 1.89 (s, 3H), 2.28-2.31 (m, 2H), 2.35 (s, 3H), 2.40 (s, 3H), 2.65 (t, 2H), 2.73-2.87 (m, 2H), 3.17 (t, 2H), 3.24 (s, 3H), 3.45 (t, 2H), 5.37 (m, 1H), 6.79 (s, 1H), 7.11 (s, 1H), 7.66 (d, 2H), 7.93 (d, 2H), 8.24 (s, 1H), 10.59 (s, 2H); RP-HPLC Rt 11.607 min, 95% 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 499 (MH+).

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