Diethyl Ether → 2-Amino-9-(2-formyloxyethoxymethyl)adenine

HRID 848100Notes

Reaction equation

HRID 848100 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][OH:15])=[C:4]([NH2:16])[N:3]=1.C[CH2:18][O:19]CC>C(O)=O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][O:15][CH:18]=[O:19])=[C:4]([NH2:16])[N:3]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 945882,6-Diamino-9-(2-hydroxyethoxymethyl)purine

Product 1

HCID 132555722-Amino-9-(2-formyloxyethoxymethyl)adenine

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 2-amino-9-(2-hydroxyethoxymethyl)adenine (0.5 g) in 97% formic acid (2.5 ml) was stirred in an ice bath for 3 hours, and then at room temperature overnight. Dry ether (80 ml) was added and the mixture chilled. The solid was removed by filtration and dissolved in hot acetonitrile (125 ml); residual solids were removed by filtration. The filtrate was applied to a column containing silica gel (14 g) in acetonitrile. The column was eluted with dry acetone. The eluate was evaporated and the residual solid recrystallized from acetonitrile to give 2-amino-9-(2-formyloxyethoxymethyl)adenine (93 mg, m.p. 238°-240° C.).

Workup

  1. customat room temperature
  2. customovernight
  3. temperaturethe mixture chilled
  4. customThe solid was removed by filtration
  5. dissolutiondissolved in hot acetonitrile (125 ml)
  6. customresidual solids were removed by filtration
  7. additioncontaining silica gel (14 g) in acetonitrile
  8. washThe column was eluted with dry acetone
  9. customThe eluate was evaporated
  10. customthe residual solid recrystallized from acetonitrile

Sources & evidence

ORD record
ord-4cab48eb95094fc29a0e731b76fd03d6
Source dataset
uspto-grants-1981_10
Patent number
US04294831

Reaction notes

Loading…