Sodium hydride → 3-iodo-1-((8-methyl-2-(2-(trifluoro-methyl)phenyl)quinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 2074493Notes

Reaction equation

HRID 2074493 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.[H-].[Na+].Cl[CH2:15][C:16]1[C:17]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]([F:36])([F:35])[F:34])=[N:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:26]>CN(C=O)C>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([CH2:15][C:16]2[C:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]([F:36])([F:35])[F:34])=[N:18][C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:26])[N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 57556155HCID 57556155, compoundHCID 178508725HCID 178508725, compound

Product 1

HCID 575561613-iodo-1-((8-methyl-2-(2-(trifluoro-methyl)phenyl)quinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Prepared according to Procedure I using 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.41 g, 1.6 mmol, 1 eq) in DMF (5 mL), NaH (60%, 0.138 g, 3.5 mmol, 2.2 eq), and 3-(chloromethyl)-8-methyl-2-(2-(trifluoromethyl)phenyl)quinoline (0.58 g, 1.7 mmol, 1 eq) in DMF (3 mL). After purification, 3-iodo-1-((8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine was obtained as white solid. 1H NMR (DMSO-d6) δ ppm 8.27 (1 H, s), 7.99 (1 H, s), 7.88 (1 H, d, J=7.8 Hz), 7.73-7.79 (1 H, m), 7.65 (1 H, d, J=6.7 Hz), 7.51-7.61 (3 H, m), 7.28-7.35 (1 H, m), 5.41-5.54 (2 H, m), 2.60 (3 H, s). Mass Spectrum (ESI) m/e=561.0 (M+1).

Workup

  1. customPrepared
  2. customAfter purification

Sources & evidence

ORD record
ord-63eb76d5cd574734b043822252970dbc
Source dataset
uspto-grants-2011_04
Patent number
US07919498B2

Reaction notes

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