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

HRID 2424824Notes

Reaction equation

HRID 2424824 reaction equation
C[C@@H]1CN(CC2C=NC(C)=NC=2)C[C@H]1C1NC(=O)C2C=NN(C3CCOCC3)C=2N=1.Cl.[CH2:32]([C@@H:34]1[CH2:38][NH:37][CH2:36][C@H:35]1[C:39]1[NH:40][C:41](=[O:54])[C:42]2[CH:47]=[N:46][N:45]([CH:48]3[CH2:53][CH2:52][O:51][CH2:50][CH2:49]3)[C:43]=2[N:44]=1)[CH3:33].C([BH3-])#N.[Na+].[CH3:59][O:60][C:61]1[CH:68]=[CH:67][C:64]([CH:65]=O)=[CH:63][N:62]=1>>[CH2:32]([C@@H:34]1[CH2:38][N:37]([CH2:65][C:64]2[CH:63]=[N:62][C:61]([O:60][CH3:59])=[CH:68][CH:67]=2)[CH2:36][C@H:35]1[C:39]1[NH:40][C:41](=[O:54])[C:42]2[CH:47]=[N:46][N:45]([CH:48]3[CH2:49][CH2:50][O:51][CH2:52][CH2:53]3)[C:43]=2[N:44]=1)[CH3:33]

Participants

5

Reactant 4

HCID 33645766-Methoxypyridine-3-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 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 1363442016-[(3S,4S)-4-ethylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrogen chloride

Product 1

HCID 1358865116-{(3S,4S)-4-ethyl-1-[(6-methoxypyridin-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-[(3S,4S)-4-ethylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrogen chloride, sodium cyanoborohydride and 6-methoxynicotinaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 8.04 (d, J=2.1 Hz, 1H), 8.02 (s, 1H), 7.73-7.71 (m, 1H), 6.78 (d, J=8.7 Hz, 1H), 4.80-4.75 (m, 1H), 4.12-4.10 (m, 2H), 3.92-3.90 (m, 3H), 3.72-3.70 (m, 1H), 3.61-3.54 (m, 3H), 3.32 (t, J=8.3 Hz, 1H), 2.99 (m, 1H), 2.91 (m, 1H), 2.41 (m, 1H), 2.40-2.28 (m, 2H), 2.21 (m, 1H), 1.95 (m, 1H), 1.91-1.83 (m, 2H), 1.65-1.45 (m, 2H), 0.92 (t, J=7.5 Hz, 3H). MS: (M+H m/z 439.2).

Sources & evidence

ORD record
ord-a8e91f0efb8d485ab319e68697bad48e
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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