2,4-Difluorobenzaldehyde → HCID 135886499, compound

HRID 2424814Notes

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]1[CH:43]=[C:42]([F:44])[CH:41]=[CH:40][C:37]=1[CH:38]=O>>[F:35][C:36]1[CH:43]=[C:42]([F:44])[CH:41]=[CH:40][C:37]=1[CH2:38][N:5]1[CH2:6][C@@H:2]([CH3:1])[C@H:3]([C:15]2[NH:16][C:17](=[O:30])[C:18]3[CH:23]=[N:22][N:21]([CH:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[C:19]=3[N:20]=2)[CH2:4]1

Participants

Reactant 3

HCID 737702,4-Difluorobenzaldehyde

HCID 5003444Sodium cyanoborohydride

HCID 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 135886499HCID 135886499, compound

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 2,4-difluorobenzaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 8.01 (s, 1H), 7.40-7.38 (m, 2H), 6.90-6.79 (m, 2H), 4.81-4.77 (m, 2H), 4.14-4.08 (m, 2H), 3.88 (m, 2H), 3.62-3.54 (m, 2H), 3.32 (t, J=8.7 Hz, 1H), 3.02 (d, J=9.5 Hz, 1H), 2.86-2.83 (m, 1H), 2.65 (m, 1H), 2.43-2.20 (m, 3H), 2.00-1.83 (m, 2H), 1.21 (d, J=6.6 Hz, 3H). MS: (M+H m/z 430.2).

Sources & evidence

ORD record: ord-15819ec47a464c18991a080265d9625f
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964607B2

Reaction notes

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