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

HRID 2424822Notes

Reaction equation

HRID 2424822 reaction equation
C[C@@H]1CNC[C@H]1C1NC(=O)C2C=NN(C3CCOCC3)C=2N=1.C([N:30]1[CH2:34][C@@H:33]([CH2:35][CH3:36])[C@H:32]([C:37]2[NH:38][C:39](=[O:52])[C:40]3[CH:45]=[N:44][N:43]([CH:46]4[CH2:51][CH2:50][O:49][CH2:48][CH2:47]4)[C:41]=3[N:42]=2)[CH2:31]1)C1C=CC=CC=1>>[CH2:35]([C@@H:33]1[CH2:34][NH:30][CH2:31][C@H:32]1[C:37]1[NH:38][C:39](=[O:52])[C:40]2[CH:45]=[N:44][N:43]([CH:46]3[CH2:47][CH2:48][O:49][CH2:50][CH2:51]3)[C:41]=2[N:42]=1)[CH3:36]

Participants

3

Reactant 2

HCID 1358864916-[(3S,4S)-1-benzyl-4-ethylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-oneHCID 1361285606-[(3S,4S)-4-methylpyrrolidin-3-yl]-1-tetrahydropyran-4-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one

Product 1

HCID 1361285286-[(3S,4S)-4-ethylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

Procedure

Following the procedure for the preparation of 6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one but substituting 6-[(3S,4S)-1-benzyl-4-ethylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one provided the title compound. 400 MHz 1H NMR (CD3OD) δ 8.02 (s, 1H), 4.97 (m, 1H), 4.09-4.06 (m, 2H), 3.78-3.58 (m, 4H), 3.34-3.34 (m, 1H), 3.16-3.11 (m, 1H), 2.68 (d, J=8.7 Hz, 1H), 2.63 (m, 1H), 2.32-2.27 (m, 2H), 1.90-1.87 (m, 2H), 1.69 (m, 1H), 1.57 (m, 1H), 0.97 (t, J=7.5 Hz, 3H). MS: (M+H m/z 318.2).

Sources & evidence

ORD record
ord-22ecbabb3fa04ace8dd4828662749bf9
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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