Potassium Carbonate → 2-Chloro-9-(3-methoxycarbonylmethylbenzyl)adenine

HRID 1684970Notes

Reaction equation

HRID 1684970 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH2:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]1[CH:21]=[C:22]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH:23]=[CH:24][CH:25]=1>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH:21]=2)=[C:4]([NH2:11])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 949042-ChloroadenineHCID 10014651(3-Bromomethyl-phenyl)-acetic acid methyl ester

Product 1

HCID 230794762-Chloro-9-(3-methoxycarbonylmethylbenzyl)adenineYield 64.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Chloroadenine (1.70 g, 10.0 mmol) and potassium carbonate (9.67 g, 70.0 mmol) were added to DMF (35 ml) and the mixture was stirred at 60° C. for 1.5 hours. After cooling to room temperature, methyl 3-bromomethylphenylacetate (3.16 g, 13.0 mmol) was added thereto and the mixture was stirred at room temperature for 1.5 hours. After removing the solvent, thereto was added chloroform (50 ml) and the resulting solid was washed with water to give the captioned compound (2.13 g, 6.41 mmol, yield: 64%) as a pale yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringthe mixture was stirred at room temperature for 1.5 hours
  3. customAfter removing the solvent
  4. additionwas added chloroform (50 ml)
  5. washthe resulting solid was washed with water

Sources & evidence

ORD record
ord-e56bf7871cdf4d5d96c7faf6c4e155ce
Source dataset
uspto-grants-2012_04
Patent number
US08148371B2

Reaction notes

Loading…