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

HRID 614947Notes

Reaction equation

HRID 614947 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-034e2eed0f2043c38cd9647d1dcc99bb
Source dataset
uspto-grants-1979_03
Patent number
US04146715

Reaction notes

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