6-Methyl-3-pyridinecarboxaldehyde → 6-{(3S,4S)-4-methyl-1-[(6-methylpyridin-3-yl)methyl]pyrrolidin-3-yl}-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 2424798Notes

Reaction equation

HRID 2424798 reaction equation
[CH3:1][C@@H:2]1[CH2:6][N:5]([CH2:7][C:8]2[CH:9]=[N:10][C:11]([CH3:14])=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.[CH3:31]C1C=CC(C=O)=CN=1>>[CH3:1][C@@H:2]1[CH2:6][N:5]([CH2:7][C:8]2[CH:9]=[N:10][C:11]([CH3:31])=[CH:14][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

Participants

3

Reactant 2

HCID 101925666-Methyl-3-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-one

Product 1

HCID 1358864676-{(3S,4S)-4-methyl-1-[(6-methylpyridin-3-yl)methyl]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 6-methylnicotinaldehyde provided the title compound. 400 MHz 1H NMR (CD3OD) δ 8.38 (d, J=2.1 Hz, 1H), 7.99 (s, 1H), 7.77 (d, J=2.07 Hz, 1H), 7.75 (d, J=2.07 Hz, 1H), 4.94-4.83 (m, 1H), 4.09-4.05 (m, 2H), 3.78-3.57 (m, 4H), 3.31-3.28 (m, 1H), 3.11-3.06 (m, 1H), 3.01-2.91 (m, 2H), 2.72-2.65 (m, 1H), 2.50 (s, 3H), 2.33-2.23 (m, 3H), 1.90-1.86 (m, 2H), 1.14 (d, J=7.1 Hz, 3H). MS: (M+H m/z 409.2).

Sources & evidence

ORD record
ord-c85ceb4966594cf4af7f43fa4dfa7bbc
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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