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

HRID 2424811Notes

Reaction equation

[CH3:1][C@@H:2]1[CH2:6][N:5]([CH2:7][C:8]2[CH:9]=NC(C)=N[CH:13]=2)[CH2:4][C@H:3]1[C:15]1[NH:16][C:17](=[O:30])[C:18]2[CH:23]=[N:22][N:21]([CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[C:19]=2[N:20]=1.C([BH3-])#N.[Na+].[F:35][C:36]1[CH:43]=CC(C=O)=C[CH:37]=1>>[F:35][C:36]1[CH:43]=[CH:13][C:8]([CH2:7][N:5]2[CH2:6][C@@H:2]([CH3:1])[C@H:3]([C:15]3[NH:16][C:17](=[O:30])[C:18]4[CH:23]=[N:22][N:21]([CH:24]5[CH2:25][CH2:26][O:27][CH2:28][CH2:29]5)[C:19]=4[N:20]=3)[CH2:4]2)=[CH:9][CH:37]=1

Participants

Reactant 3

HCID 680234-Fluorobenzaldehyde

HCID 5003444Sodium cyanoborohydride

HCID 1358864606-((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

Product 1

HCID 1358864896-[(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

Procedure

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).

Sources & evidence

ORD record: ord-d31402b1e35944f2af0158ce1211b45d
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964607B2

Reaction notes

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