6-Methoxypyridine-3-carbaldehyde → 1-isopropyl-6-{(3S,4S)-1-[(6-methoxypyridin-3-yl)methyl]-4-methylpyrrolidin-3-yl}1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 2424775Notes

Reaction equation

HRID 2424775 reaction equation
[CH:1]([N:4]1[C:8]2[N:9]=[C:10]([C@H:14]3[C@H:18]([CH3:19])[CH2:17][NH:16][CH2:15]3)[NH:11][C:12](=[O:13])[C:7]=2[CH:6]=[N:5]1)([CH3:3])[CH3:2].[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][N:23]=1>>[CH:1]([N:4]1[C:8]2[N:9]=[C:10]([C@H:14]3[C@H:18]([CH3:19])[CH2:17][N:16]([CH2:26][C:25]4[CH:24]=[N:23][C:22]([O:21][CH3:20])=[CH:29][CH:28]=4)[CH2:15]3)[NH:11][C:12](=[O:13])[C:7]=2[CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 33645766-Methoxypyridine-3-carbaldehydeHCID 1361284601-isopropyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

Product 1

HCID 1358759191-isopropyl-6-{(3S,4S)-1-[(6-methoxypyridin-3-yl)methyl]-4-methylpyrrolidin-3-yl}1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Procedure

Following the procedure for the preparation of 1-cyclopentyl-6-[(3,4-trans)-4-methyl-1-(pyridin-3-ylmethyl)pyrrolidin-3-yl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one but substituting 1-isopropyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one and 6-methoxynicotinaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 8.02 (s, 2H), 7.72 (m, 1H), 6.77 (d, J=8.3 Hz, 1H), 3.90 (s, 3H), 3.73-3.53 (m, 2H), 3.39-3.33 (m, 1H), 3.30 (m, 1H), 2.8 (m, 1H), 2.55-2.40 (m, 1H), 1.9 (m, 1H), 1.57-1.53 (m, 2H), 1.52-1.47 (m, 6H), 1.19 (d, J=6.6 Hz, 3H). MS: (M+H m/z=383.2).

Sources & evidence

ORD record
ord-7f80667ed84b4d9c974cce4f31b5e11f
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

Loading…