Triethylamine → 6-Chloro-9-(2-benzoyloxyethoxymethyl)purine

HRID 2285543Notes

Reaction equation

HRID 2285543 reaction equation
[C:1]([O:9][CH2:10][CH2:11][O:12][CH2:13]Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:15][C:16]1[N:24]=[CH:23][N:22]=[C:21]2[C:17]=1[NH:18][CH:19]=[N:20]2.C(N(CC)CC)C>CN(C)C=O>[Cl:15][C:16]1[N:24]=[CH:23][N:22]=[C:21]2[C:17]=1[N:18]=[CH:19][N:20]2[CH2:13][O:12][CH2:11][CH2:10][O:9][C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27245002-(Chloromethoxy)ethyl benzoateHCID 53592776-Chloropurine

Product 1

HCID 129267736-Chloro-9-(2-benzoyloxyethoxymethyl)purine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following substantially the procedure of Schaeffer, et al. supra but with minor modifications, 1-benzoyloxy-2-chloromethoxyethane (4.4 g) was added with stirring to a dry solution of 6-chloropurine (3.1 g) and triethylamine (6.5 ml) in dimethylformamide (50 ml). The reaction was exothermic, immediately precipitating, triethylamine hydrochloride. The reaction mixture was stirred at room temperature for 24 hours and filtered. The filtrate was evaporated on a rotary evaporator at 70° C. The remaining thick amber oil was dissolved in the minimum amount of benzene and purified by column chromatography using a silica gel column. Benzene elution removed a trace of an unidentified material. Elution with ether first remove a small amount of ethylene glycol monobenzoate then 6-chloro-9-(2-benzoyloxyethoxymethyl)purine. Recrystallization from ether gave a white material, m.p. 108.5°-111° C.

Workup

  1. customimmediately precipitating
  2. filtrationfiltered
  3. customThe filtrate was evaporated on a rotary evaporator at 70° C
  4. dissolutionThe remaining thick amber oil was dissolved in the minimum amount of benzene
  5. custompurified by column chromatography
  6. washBenzene elution
  7. customremoved a trace of an unidentified material
  8. washElution with ether
  9. customfirst remove a small amount of ethylene glycol monobenzoate
  10. customRecrystallization from ether
  11. customgave a white material, m.p. 108.5°-111° C.

Sources & evidence

ORD record
ord-ebaf67231bd74351a0be006d284b6748
Source dataset
uspto-grants-1982_04
Patent number
US04323573

Reaction notes

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