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

HRID 2424797Notes

Reaction equation

HRID 2424797 reaction equation
[CH3:1][C@@H:2]1[CH2:6][N:5]([CH2:7]C2C=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.[CH3:31][C:32]1[N:37]=[C:36](C=O)[CH:35]=[CH:34][N:33]=1>>[CH3:1][C@@H:2]1[CH2:6][N:5]([CH2:7][C:34]2[CH:35]=[CH:36][N:37]=[C:32]([CH3:31])[N:33]=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 220629452-Methylpyrimidine-4-carbaldehydeHCID 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 1358864626-{(3S,4S)-4-methyl-1-[(2-methylpyrimidin-4-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 2-methylpyrimidine-4-carbaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 8.59 (d, J=5.0 Hz, 1H), 8.03 (s, 1H), 7.20 (d, J=5.0 Hz, 1H), 4.84-4.76 (m, 1H), 4.13-4.08 (m, 2H), 3.97-3.93 (m, 1H), 3.70-3.67 (m, 1H), 3.61-3.53 (m, 2H), 3.40 (t, J=8.3 Hz, 1H), 3.14 (d, J=9.5 Hz, 1H), 2.88 (m, 1H), 2.72 (s, 3H), 2.69-2.63 (m, 1H), 2.47-2.27 (m, 3H), 2.10-2.08 (m, 1H), 1.91-1.83 (m, 2H), 1.21 (d, J=7.1 Hz, 3H). MS: (M+H m/z 410.2).

Sources & evidence

ORD record
ord-b3deed7768d64894860d33eabd2d85bd
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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