Potassium Carbonate → diethyl 4-((6-amino-2-chloro-9H-purin-9-yl)methyl)benzylphosphonate

HRID 629929Notes

Reaction equation

HRID 629929 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([NH2:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]1[CH:34]=[CH:33][C:23]([CH2:24][P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])=[CH:22][CH:21]=1>CN(C=O)C>[NH2:11][C:4]1[N:3]=[C:2]([Cl:1])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[CH2:19][C:20]1[CH:34]=[CH:33][C:23]([CH2:24][P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14750222Phosphonic acid, [[4-(bromomethyl)phenyl]methyl]-, diethyl esterHCID 178508452HCID 178508452, compound

Product 1

HCID 86667757diethyl 4-((6-amino-2-chloro-9H-purin-9-yl)methyl)benzylphosphonateYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of commercially available 2-chloro-9H-purin-6-amine (1 equiv.) in DMF (0.50 M) was added potassium carbonate (1.2 equiv.) and diethyl 4-(bromomethyl)benzylphosphonate (1 equiv.) (described in ref. 88, Ex 25 Step 1). The reaction mixture was then heated to 60° C. for 5 h. At this point the reaction mixture was allowed to cool to room temperature and the volatiles were removed in vacuo. The resulting residue was purified by a COMBIFLASH™ system (ISCO) using a gradient of 0-5% MeOH/DCM to provide the title compound (18%) as a solid.

Workup

  1. temperatureto cool to room temperature
  2. customthe volatiles were removed in vacuo
  3. customThe resulting residue was purified by a COMBIFLASH™ system (ISCO)

Sources & evidence

ORD record
ord-bc91674a6e3e4837bd238584403a03e9
Source dataset
uspto-grants-2016_04
Patent number
US09315530B2

Reaction notes

Loading…