5-Methylpyrazine-2-carboxaldehyde → 1-isopropyl-6-{(3S,4S)-4-methyl-1-[(5methylpyrazin-2-yl)methyl]pyrrolidin-3-yl}-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 2424778Notes

Reaction equation

HRID 2424778 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][C:21]1[N:22]=[CH:23][C:24]([CH:27]=O)=[N:25][CH:26]=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]([CH2:20][C:21]4[CH:26]=[N:25][C:24]([CH3:27])=[CH:23][N:22]=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 136249775-Methylpyrazine-2-carboxaldehydeHCID 1361284601-isopropyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

Product 1

HCID 1358864571-isopropyl-6-{(3S,4S)-4-methyl-1-[(5methylpyrazin-2-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-isopropyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one and 5-methylpyrazine-2-carbaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 11.4 (brs, 1H), 8.49 (s, 1H), 8.44 (s, 1H), 7.99 (s, 1H), 5.00-4.93 (m, 1H), 4.00-3.97 (m, 1H), 3.78-3.67 (m, 1H), 3.33 (t, J=8.3 Hz, 1H), 3.04 (d, J=9.9 Hz, 1H), 2.85-2.82 (m, 1H), 2.65-2.61 (m, 1H), 2.49 (s, 3H), 2.48-2.41 (m, 1H), 2.13 (t, J=8.5 Hz, 1H), 1.46 (dd, J=11.6,6.6 Hz, 6H), 1.17 (d, J=7.05 Hz, 3H). MS: (M+H m/z=368.1).

Sources & evidence

ORD record
ord-806f78e7633240e6a563abf57e6355f2
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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