Adenine → 2-(6-Aminopurin-9-yl)ethanol

HRID 439586

Reaction equation

HRID 439586 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.C1(=O)O[CH2:14][CH2:13][O:12]1.[OH-].[Na+].C1(C)C=CC=CC=1>CN(C=O)C>[OH:12][CH2:13][CH2:14][N:5]1[CH:6]=[N:7][C:8]2[C:4]1=[N:3][CH:2]=[N:1][C:9]=2[NH2:10]

Participants

6

Reactant 4

HCID 190AdenineHCID 1140TolueneHCID 7303Ethylene carbonateHCID 14798Sodium Hydroxide

Product 1

HCID 2426522-(6-Aminopurin-9-yl)ethanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Adenine (9.1 g), ethylene carbonate (6.0 g), and sodium hydroxide (0.14 g) in DMF (68 ml) were heated at reflux for 2 hr The solution was cooled to 0°, then 70 ml of toluene were added. After sitting for 2 hr at 0°, the precipitate was collected, rinsed with 100 ml of toluene, then cold ethanol, and dried to afford N9 -hydroxyethyladenine.

Workup

  1. temperatureat reflux for 2 hr The solution
  2. temperaturewas cooled to 0°
  3. customthe precipitate was collected
  4. washrinsed with 100 ml of toluene
  5. dry with materialcold ethanol, and dried

Sources & evidence

ORD record
ord-bf4567b048f14c1da63f8477b7c5abad
Source dataset
uspto-grants-1996_05
Patent number
US05514798

Linked notes

Loading…