Sodium Carbonate → 3-(4-Amino-1-((8-chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol

HRID 2074506Notes

Reaction equation

HRID 2074506 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:8]([CH2:19][N:20]1[C:24]3=[N:25][CH:26]=[N:27][C:28]([NH2:29])=[C:23]3[C:22](I)=[N:21]1)=[CH:7]2.[C:31](=[O:34])([O-])[O-].[Na+].[Na+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:29][C:28]1[N:27]=[CH:26][N:25]=[C:24]2[N:20]([CH2:19][C:8]3[C:9]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[Cl:18])=[N:10][C:11]4[C:6]([CH:7]=3)=[CH:5][CH:4]=[CH:3][C:2]=4[Cl:1])[N:21]=[C:22]([C:11]3[CH:6]=[C:31]([OH:34])[CH:4]=[CH:3][CH:2]=3)[C:23]=12

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 575561871-((8-chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 575561533-(4-Amino-1-((8-chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Prepared according to Procedure J using 1-((8-chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.100 g, 0.18 mmol), 3-(hydroxyphenyl)boronic acid (0.050 g, 0.37 mmol, 2 eq), tetrakis(triphenylphosphine)palladium (0.021 g, 0.018 mmol, 0.1 eq) and 2M aq sodium carbonate (0.54 mL, 1.08 mmol, 6 eq) in DMF (1 mL). 3-(4-Amino-1-((8-chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol [PI3Kδ IC50=14 nM] was obtained after purification as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.52 (1 H, s), 8.31 (1 H, s), 7.91-8.00 (2 H, m), 7.86 (1 H, dd, J=7.4, 1.2 Hz), 7.52 (1 H, t, J=7.8 Hz), 7.35 (1 H, d, J=8.2 Hz), 7.07-7.28 (3 H, m), 6.97-7.05 (1 H, m), 6.78-6.93 (2 H, m), 6.70 (1 H, dd, J=8.2, 1.6 Hz), 5.36-5.57 (2 H, m) Mass Spectrum (ESI) m/e=513.1 and 515.0 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-56bc5b95f65a4d6aa4e856fcad5ec826
Source dataset
uspto-grants-2011_04
Patent number
US07919498B2

Reaction notes

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