o-(Trifluoromethyl)benzaldehyde → 6-{(3S,4S)-4-methyl-1-[2-(trifluoromethyl)benzyl]pyrrolidin-3-yl}-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 2424813Notes

Reaction equation

HRID 2424813 reaction equation
[CH3:1][C@@H:2]1[CH2:6][N:5](CC2C=NC(C)=NC=2)[CH2:4][C@H:3]1[C:15]1[NH:16][C:17](=[O:30])[C:18]2[CH:23]=[N:22][N:21]([CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[C:19]=2[N:20]=1.C([BH3-])#N.[Na+].[F:35][C:36]([F:46])([F:45])[C:37]1[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=1[CH:39]=O>>[CH3:1][C@@H:2]1[CH2:6][N:5]([CH2:39][C:38]2[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=2[C:36]([F:46])([F:45])[F:35])[CH2:4][C@H:3]1[C:15]1[NH:16][C:17](=[O:30])[C:18]2[CH:23]=[N:22][N:21]([CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[C:19]=2[N:20]=1

Participants

4

Reactant 3

HCID 123067o-(Trifluoromethyl)benzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 1358864606-((3S,4S)-4-Methyl-1-((2-methylpyrimidin-5-YL)methyl)pyrrolidin-3-YL)-1-(tetrahydro-2H-pyran-4-YL)-1,5-dihydro-4H-pyrazolo[3,4-D]pyrimidin-4-one

Product 1

HCID 1358864976-{(3S,4S)-4-methyl-1-[2-(trifluoromethyl)benzyl]pyrrolidin-3-yl}-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Procedure

Following the procedure for the preparation of 6-{(3S,4S)-4-methyl-1-[(2-methylpyrimidin-5-yl)methyl]pyrrolidin-3-yl}-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one but substituting sodium cyanoborohydride and 2-(trifluoromethyl)benzaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 10.58 (brs, 1H), 8.01 (s, 1H), 7.79-7.76 (m, 1H), 7.64-7.58 (m, 2H), 7.37-7.34 (m, 1H), 4.83-4.76 (m, 1H), 4.14-4.08 (m, 2H), 3.88 (m, 2H), 3.62-3.54 (m, 2H), 3.39 (t, J=8.3 Hz, 1H), 3.02-2.97 (m, 1H), 2.85 (m, 1H), 2.66 (m, 1H), 2.44-2.27 (m, 3H), 2.06-2.03 (m, 1H), 1.91-1.83(m,2H), 1.21 (d,J=7.1 Hz, 3H). MS: (M+H m/z 462.1).

Sources & evidence

ORD record
ord-3edbc075297d4c2481f80cb16efb70c3
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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