4-Fluorobenzaldehyde → 6-[(3S,4S)-1-(4-fluorobenzyl)-4-methylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Participants

Reaction Steps

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 sodium cyanoborohydride and 4-fluorobenzaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 8.02 (s, 1H), 7.36-7.33 (m, 2H), 7.05-7.01 (m, 2H), 4.82-4.77 (m, 1H), 4.14-4.09 (m, 2H), 3.79-3.76 (m, 1H), 3.62-3.54 (m, 3H), 3.34 (t, J=8.3 Hz, 1H), 2.99 (d, J=9.9 Hz, 1H), 2.85-2.83 (m, 1H), 2.60-2.55 (m, 1H), 2.45-2.30 (m, 3H), 1.99-1.82 (m, 3H), 1.20 (d, J=7.1 Hz, 3H). MS: (M+H m/z 412.1).

Provenance & Evidence