Triethylamine → N(6)-But-2-enyl-N(6)-(2,5-dimethylbenzyl)-adenosine

HRID 1659089Notes

Reaction equation

HRID 1659089 reaction equation
C([N:4]1[C:12]2[CH:7]([N:8](C(=O)C)[CH2:9][N:10](C(=O)C)[C:11]=2Cl)[N:6]([C@@H:20]2[O:26][C@H:25]([CH2:27][OH:28])[C@@H:23]([OH:24])[C@H:21]2[OH:22])[CH2:5]1)(=O)C.[CH2:29]([NH:33][CH2:34][C:35]1[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][C:36]=1[CH3:42])[CH:30]=[CH:31][CH3:32].C(N(CC)CC)C>C(O)(C)C>[CH2:29]([N:33]([CH2:34][C:35]1[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][C:36]=1[CH3:42])[C:11]1[C:12]2[N:4]=[CH:5][N:6]([C:7]=2[N:8]=[CH:9][N:10]=1)[C@@H:20]1[O:26][C@H:25]([CH2:27][OH:28])[C@@H:23]([OH:24])[C@H:21]1[OH:22])[CH:30]=[CH:31][CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53753187N-but-2-enyl-(2,5-dimethylbenzyl)-amineHCID 131710375Triacetyl-6-chloro-9-(beta-D-ribofuranosyl)-purine

Product 1

HCID 54027274N(6)-But-2-enyl-N(6)-(2,5-dimethylbenzyl)-adenosine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

10 g. Triacetyl-6-chloro-9-(β-D-ribofuranosyl)-purine, 5.7 g. N-but-2-enyl-(2,5-dimethylbenzyl)-amine and 2.5 g. triethylamine were heated under reflux for 1 hour in 150 ml. isopropanol. Subsequently, the solvent was removed in a vacuum and the residue taken up in chloroform. The chloroform phase was washed several times with water, dried and evaporated. The syrupy residue was dissolved in 150 ml. methanol and the solution mixed with 5 ml. 1N sodium methylate solution and then boiled for 10 minutes. Thereafter, the methanol was replaced by ethyl acetate and the ethyl acetate solution washed two or three times with water. After drying and evaporating the solution, the residue was recrystallized twice from 100 ml. methanol/water (1:1), with the addition of active charcoal. There were finally obtained 5.9 g. (56% of theory) N(6)-but-2-enyl-N(6)-(2,5-dimethylbenzyl)-adenosine, which had a melting point of 125°-127°C.

Workup

  1. temperatureunder reflux for 1 hour in 150 ml
  2. customSubsequently, the solvent was removed in a vacuum
  3. washThe chloroform phase was washed several times with water
  4. customdried
  5. customevaporated
  6. dissolutionThe syrupy residue was dissolved in 150 ml
  7. additionmethanol and the solution mixed with 5 ml
  8. washthe ethyl acetate solution washed two or three times with water
  9. customAfter drying
  10. customevaporating the solution
  11. customthe residue was recrystallized twice from 100 ml
  12. additionmethanol/water (1:1), with the addition of active charcoal

Sources & evidence

ORD record
ord-dd9b671f422440e29f4a3a49bde9f369
Source dataset
uspto-grants-1976_06
Patent number
US03966916

Reaction notes

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