m-Formylbenzonitrile → HCID 135886519, compound

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Following the procedure for the preparation of 6-{(3S,4S)-4-methyl-1-[(2-methylpyrimidin-5-yl)methyl]pyrrolidin-3-yl}-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one but substituting 6-[(3S,4S)-4-ethylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrogen chloride, sodium cyanoborohydride and 3-formylbenzonitrile provided the title compound. 400 MHz 1H NMR (CDCl3) δ 8.01 (s, 1H), 7.73-7.41 (m, 4H), 4.79 (m, 1H), 4.72 (s, 1H), 4.12-4.09 (m, 2H), 3.82-3.70 (m, 2H), 3.61-3.54 (m, 2H), 3.27 (t, J=8.3 Hz, 1H), 3.02-2.97 (m, 2H), 2.71-2.70 (m, 1H), 2.37-2.30 (m, 2H), 2.20-2.14 (m, 1H), 1.90-1.87 (m, 2H), 1.61-1.60 (m, 1H), 1.51-1.49 (m, 1H), 0.91 (t, J=7.5 Hz, 3H). MS: (M+H m/z 433.2).

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