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

HRID 614921Notes

Reaction equation

HRID 614921 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.Cl.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

6

Reactant 4

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 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 (4.4g) was added with stirring to a dry solution of 6-chloropurine (3.1g) and triethylamine (6.5ml) in dimethylformamide (50ml). 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 removed a small amount of ethylene glycol monobenzoate and then 6-chloro-9-(2-benzoyloxyethoxymethyl)purine. Recrystallization from ether gave a white material, m.p. 108.5°-111° C.

Workup

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

Sources & evidence

ORD record
ord-cea871e460ac4501952a24f5d318f434
Source dataset
uspto-grants-1979_03
Patent number
US04146715

Reaction notes

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