Adenine → 9-((2-(2-Chlorophenyl)-8-methylquinolin-3-yl)methyl)-9H-purin-6-amine

HRID 2074490Notes

Reaction equation

HRID 2074490 reaction equation
Br[CH2:2][C:3]1[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][C:7]=2[CH3:13].BrCC1C(C2C=CC=CC=2C)=NC2C(C=1)=CC=CC=2C.[N:41]1[C:49]([NH2:50])=[C:48]2[C:44]([N:45]=[CH:46][NH:47]2)=[N:43][CH:42]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:4]1[C:3]([CH2:2][N:45]2[CH:46]=[N:47][C:48]3[C:44]2=[N:43][CH:42]=[N:41][C:49]=3[NH2:50])=[CH:12][C:11]2[C:6](=[C:7]([CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

6

Reactant 4

HCID 190AdenineHCID 10796Cesium carbonateHCID 575561693-(Bromomethyl)-2-(2-chlorophenyl)-8-methylquinolineHCID 577080653-(Bromomethyl)-8-methyl-2-(2-methylphenyl)quinoline

Product 1

HCID 250955109-((2-(2-Chlorophenyl)-8-methylquinolin-3-yl)methyl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(bromomethyl)-2-(2-chlorophenyl)-8-methylquinoline (66 mg, 0.19 mmol), {prepared in a similar way as 3-(bromomethyl)-8-methyl-2-o-tolylquinoline, example 9} adenine (39 mg, 0.29 mmol), and cesium carbonate (124 mg, 0.38 mmol) in DMF (0.7 mL) was stirred at rt for 2 h. The crude mixture was evaporated onto silica gel and purified by flash chromatography (Biotage Si 25+M) eluting with MeOH/CH2Cl2 (5% to 10%). The resulting white solid was further purified by HPLC (Berger SFC) eluting with i-PrOH/CO2/DEA to provide a white solid [PI3Kδ IC50=2130 nM]. MS (ESI+) m/z=401.1 (M+1).

Workup

  1. customThe crude mixture was evaporated onto silica gel
  2. custompurified by flash chromatography (Biotage Si 25+M)
  3. washeluting with MeOH/CH2Cl2 (5% to 10%)
  4. customThe resulting white solid was further purified by HPLC (Berger SFC)
  5. washeluting with i-PrOH/CO2/DEA
  6. customto provide a white solid [PI3Kδ IC50=2130 nM]

Sources & evidence

ORD record
ord-fe931b7ed25c438c8b88ffb427c02b16
Source dataset
uspto-grants-2011_04
Patent number
US07919498B2

Reaction notes

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