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

HRID 2424808Notes

Reaction equation

HRID 2424808 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]([CH3:35])[C@H:32]([C:36]2[NH:37][C:38](=[O:52])[C:39]3[C:44]([CH3:45])=[N:43][N:42]([CH:46]4[CH2:51][CH2:50][O:49][CH2:48][CH2:47]4)[C:40]=3[N:41]=2)[CH2:31]1)C1C=CC=CC=1>>[CH3:45][C:44]1[C:39]2[C:38](=[O:52])[NH:37][C:36]([C@H:32]3[C@H:33]([CH3:35])[CH2:34][NH:30][CH2:31]3)=[N:41][C:40]=2[N:42]([CH:46]2[CH2:51][CH2:50][O:49][CH2:48][CH2:47]2)[N:43]=1

Participants

3

Reactant 2

HCID 1358864816-[(3S,4S)-1-benzyl-4-methylpyrrolidin-3-yl]-3-methyl-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 1361285673-methyl-6-[(3S,4S)-4-methylpyrrolidin-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-methylpyrrolidin-3-yl]-3-methyl-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 (CDCl3) δ 4.85-4.81 (m, 1H), 4.08-4.04 (m, 2H), 3.61-3.55 (m, 2H), 3.31-3.28 (m, 3H), 2.84-2.82 (m, 1H), 2.60-2.53 (m, 2H), 2.49 (s, 3H), 2.29-2.25 (m, 2H), 1.85-1.81 (m, 2H), 1.12 (d, J=6.62 Hz, 3H). MS: (M+H m/z=249.1).

Sources & evidence

ORD record
ord-d23a57a50ad140179338d23006aef689
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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