Sodium Carbonate → 1-((8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methyl)-3-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 2074507Notes

Reaction equation

HRID 2074507 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([CH2:12][C:13]2[C:14]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]([F:33])([F:32])[F:31])=[N:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:23])[N:3]=1.[NH:34]1[CH:38]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH:36]=[N:35]1.C(=O)([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>[CH3:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:16]=1[N:15]=[C:14]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]([F:33])([F:32])[F:31])[C:13]([CH2:12][N:4]1[C:5]3=[N:6][CH:7]=[N:8][C:9]([NH2:11])=[C:10]3[C:2]([C:37]3[CH:38]=[N:34][NH:35][CH:36]=3)=[N:3]1)=[CH:22]2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 575561613-iodo-1-((8-methyl-2-(2-(trifluoro-methyl)phenyl)quinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 1361281681-((8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methyl)-3-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Prepared according to Procedure J using 3-iodo-1-((8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.1000 g, 0.178 mmol, 1 eq), pyrazole-4-boronic acid pinacol ester (0.0693 g, 0.357 mmol, 2.0 eq), tetrakis(triphenylphosphine)palladium(0) (0.0206 g, 0.0178 mmol, 10 mol %), and sodium carbonate (2M aq. sol, 0.535 mL, 1.07 mmol, 6 eq) in DMF (1 mL). After purification, 1-((8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methyl)-3-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine was obtained as white solid. The white solid was suspended in CH2Cl2 and filtered to give the desired product as white solid [PI3Kδ IC50=8 nM]. 1H NMR (DMSO-d6) δ ppm 13.17 (1 H, s), 8.22 (1 H, s), 7.97-8.08 (2 H, m), 7.71-7.90 (3 H, m), 7.56-7.66 (3 H, m), 7.52 (1 H, dd, J=7.8, 7.0 Hz), 7.35-7.44 (1H, m), 6.82 (2 H, br. s.), 5.42-5.55 (2 H, m), 2.60 (3 H, s). Mass Spectrum (ESI) m/e=501.1 (M+1).

Workup

  1. customPrepared
  2. customAfter purification

Sources & evidence

ORD record
ord-eb998800b57a49b09e87cea0139abaf0
Source dataset
uspto-grants-2011_04
Patent number
US07919498B2

Reaction notes

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