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

HRID 2424780Notes

Reaction equation

HRID 2424780 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([C@H:16]4[C@H:20]([CH3:21])[CH2:19][NH:18][CH2:17]4)[NH:13][C:14](=[O:15])[C:9]=3[CH:8]=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:22][C:23]1[N:28]=[C:27]([CH:29]=O)[CH:26]=[CH:25][N:24]=1>>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([C@H:16]4[C@H:20]([CH3:21])[CH2:19][N:18]([CH2:29][C:27]5[CH:26]=[CH:25][N:24]=[C:23]([CH3:22])[N:28]=5)[CH2:17]4)[NH:13][C:14](=[O:15])[C:9]=3[CH:8]=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 220629452-Methylpyrimidine-4-carbaldehydeHCID 1361284551-cyclopentyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

Product 1

HCID 1358759091-cyclopentyl-6-{(3S,4S)-4-methyl-1-[(2-methylpyrimidin-4-yl)methyl]pyrrolidin-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-cyclopentyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one and 2-methylpyrimidine-4-carbaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 8.60 (d, J=5.4 Hz, 1H), 8.03 (s, 1H), 7.24 (s, 1H), 5.18-5.10 (m, 1H), 3.97-3.94 (m, 1H), 3.72-3.68 (m, 1H), 3.40 (t, J=8.3 Hz, 1H), 3.15 (d, J=9.5 Hz, 1H), 2.89 (m, 1H), 2.73 (s, 3H), 2.68-2.63 (m, 1H), 2.53-2.47 (m, 1H), 2.15-1.89 (m, 7H), 1.74-1.65 (m, 2H), 1.21 (d, J=7.1 Hz, 3H). MS: (M+H m/z=394.1).

Sources & evidence

ORD record
ord-c64a65ae1cd849cc81ed7191b2a06341
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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