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

HRID 2424819Notes

Reaction equation

[CH3:1][C@@H:2]1[CH2:6][N:5](CC2C=NC(C)=NC=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+].[CH3:35][O:36][C:37]1[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=1[CH:39]=O>>[CH3:35][O:36][C:37]1[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=1[CH2:39][N:5]1[CH2:6][C@@H:2]([CH3:1])[C@H:3]([C:15]2[NH:16][C:17](=[O:30])[C:18]3[CH:23]=[N:22][N:21]([CH:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[C:19]=3[N:20]=2)[CH2:4]1

Participants

Reactant 3

HCID 86582-Methoxybenzaldehyde

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 1358865006-[(3S,4S)-1-(2-methoxybenzyl)-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 cyano borohydride and 2-methoxybenzaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 8.00 (s, 1H), 7.29-7.22 (m, 2H), 6.92-6.88 (m, 2H), 4.83-4.75 (m, 1H), 4.14-4.08 (m, 2H), 3.93 (s, 3H), 3.76-3.69 (m, 2H), 3.62-3.54 (m, 2H), 3.34 (t, J=8.7 Hz, 1H), 3.01 (d, J=9.5 Hz, 1H), 2.78 (m, 1H), 2.56 (m, 1H), 2.41-2.27 (m, 3H), 1.92-1.82 (m, 3H), 1.18 (d, J=7.1 Hz, 3H). MS: (M+H m/z 424.1).

Sources & evidence

ORD record: ord-ead00ca5ba7949a99c9e25f067e7e919
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964607B2

Reaction notes

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