Water → Guanine

HRID 2239233Notes

Reaction equation

HRID 2239233 reaction equation
[CH:1]1[NH:2][C:3]2[N:9]=[C:8]([NH2:10])[N:7]=[C:6](Cl)[C:4]=2[N:5]=1.C(N(CC)CC)C.C[O-:20].[Na+].O>C(O)C>[NH:7]1[C:6](=[O:20])[C:4]2[NH:5][CH:1]=[N:2][C:3]=2[N:9]=[C:8]1[NH2:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10942334Sodium MethoxideHCID 1785084356-chloro-1H-purin-2-amine

Product 1

HCID 135398634Guanine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Chloroguanine derivative prepared in Preparation 6 (100 mg) was dissolved in 10 ml of ethanol, 32 ml of triethylamine and 53 mg of sodium methoxide were added, and the resulting mixture was refluxed for 4 hours. The reaction was stopped by adding 10 ml of water. The reaction solution was extracted with dichloromethane and distilled under reduced pressure. The residue was purified by silica gel column to give a compound wherein 6-position of guanine was substituted by ethoxy group.

Workup

  1. temperaturethe resulting mixture was refluxed for 4 hours
  2. extractionThe reaction solution was extracted with dichloromethane
  3. distillationdistilled under reduced pressure
  4. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-fb920e21ada44098a9b0fd3b9da5340a
Source dataset
uspto-grants-2010_05
Patent number
US07723319B2

Reaction notes

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