6-Methyl-2-pyridinecarboxaldehyde → HCID 135886492, compound

HRID 2424810Notes

Reaction equation

[CH3:1][C@@H:2]1[CH2:6][N:5]([CH2:7]C2C=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+].C[C:36]1[N:41]=[C:40]([CH:42]=O)[CH:39]=[CH:38][CH:37]=1>>[CH3:1][C@@H:2]1[CH2:6][N:5]([CH2:7][C:36]2[CH:37]=[CH:38][CH:39]=[C:40]([CH3:42])[N:41]=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

Participants

Reactant 3

HCID 707376-Methyl-2-pyridinecarboxaldehyde

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 135886492HCID 135886492, 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 6-methylpicolinaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 8.02 (s, 1H), 7.57 (t, J=7.7 Hz, 1H), 7.20 (d, J=7.9 Hz, 1H), 7.03 (d, J=7.5 Hz, 1H), 4.83-4.77 (m, 1H), 4.13-4.08 (m, 2H), 3.99-3.95 (m, 1H), 3.72-3.69 (m, 1H), 3.62-3.54 (m, 2H), 3.42 (t, J=8.3 Hz, 1H), 3.06 (d, J=9.9 Hz, 1H), 2.85-2.83 (m, 1H), 2.64-2.57 (m, 1H), 2.55 (s, 3H), 2.44-2.29 (m, 3H), 2.08-2.03 (m, 1H), 1.91-1.82 (m, 2H), 1.20 (t, J=7.1 Hz, 3H). MS: (M+H m/z 409.1).

Sources & evidence

ORD record: ord-f532ab84f04c4194aeafcc9de8fabc5d
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964607B2

Reaction notes

Loading…