3-Pyridinecarboxaldehyde → 3-methyl-6-[(3S,4S)-4-methyl-1-(pyridin-3-ylmethyl)pyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 2424807Notes

Reaction equation

HRID 2424807 reaction equation
[CH3:1][C@@H:2]1[CH2:6][N:5]([CH2:7][C:8]2[CH:9]=N[C:11]([CH3:14])=[N:12][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.[CH3:31]C1C2C(=O)NC([C@H]3[C@H](C)CNC3)=NC=2N(C2CCOCC2)N=1.C(=O)C1C=CC=NC=1>>[CH3:31][C:23]1[C:18]2[C:17](=[O:30])[NH:16][C:15]([C@H:3]3[C@H:2]([CH3:1])[CH2:6][N:5]([CH2:7][C:8]4[CH:13]=[N:12][CH:11]=[CH:14][CH:9]=4)[CH2:4]3)=[N:20][C:19]=2[N:21]([CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:22]=1

Participants

4

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 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-oneHCID 1361285673-methyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

Product 1

HCID 1358864873-methyl-6-[(3S,4S)-4-methyl-1-(pyridin-3-ylmethyl)pyrrolidin-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 3-methyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one and nicotinaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 8.53 (m, 2H), 7.83 (d, J=7.9 Hz, 1H), 7.36-7.33 (m, 1H), 4.74-4.68 (m, 1H), 4.12-4.07 (m, 2H), 3.79-3.76 (m, 1H), 3.68-3.65 (m, 1H), 3.59-3.52 (m, 2H), 3.47 (s, 1H), 3.34 (t, J=8.7 Hz, 1H), 2.99 (d, J=9.9 Hz, 1H), 2.82-2.80 (m, 1H), 2.61-2.57 (m, 1H), 2.54 (s, 3H), 2.42-2.28 (m, 2H), 1.95 (t, J=8.7 Hz, 1H), 1.87-1.78 (m, 2H), 1.19 (d, J=7.1 Hz, 3H). MS: (M+H m/z 409.2).

Sources & evidence

ORD record
ord-2c47970502854f09845c670db6390b59
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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