N-Allylcyclohexylamine → N-Cyclohexyl-9-pentofuranosyl-N-(prop-2-en-1-yl)-9H-purin-6-amine

HRID 328196

Reaction equation

HRID 328196 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:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[CH:30]=[CH2:31]>C(O)CCC>[CH2:29]([N:32]([CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[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]=[CH2:31]

Participants

4

Reactant 2

HCID 81115N-AllylcyclohexylamineHCID 131710375HCID 131710375, compound

Product 1

HCID 3085089N-Cyclohexyl-9-pentofuranosyl-N-(prop-2-en-1-yl)-9H-purin-6-amineYield 59%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

10 g. triacetyl-6-chloro-9-(β-D-ribofuranosyl)-purine and 10 g. allyl-cyclohexylamine were heated under reflux for 1 hour in 100 ml. butanol. The butanol was then distilled off in a vacuum, the residue was dissolved in chloroform and the chloroform solution was then shaken out successively with dilute hydrochloric acid, dilute aqueous sodium bicarbonate solution and water. The chloroform solution was then dried over anhydrous sodium sulfate and evaporated to a syrup. This was dissolved in methanol and the solution, after the addition of 5 ml. 1N sodium methylate solution was heated for 10 minutes on a steambath. After cooling, the solution was distilled off to dryness, the residue was dissolved in chloroform and the chloroform solution was washed with water. The organic phase was dried and evaporated and the residue obtained recrystallized from ethanol. 6.1 g. (59% of theory) N(6)-allyl-N(6)-cyclohexyl-adenosine were obtained; m.p. 123° - 125° C.

Workup

  1. temperatureunder reflux for 1 hour in 100 ml
  2. distillationThe butanol was then distilled off in a vacuum
  3. dissolutionthe residue was dissolved in chloroform
  4. dry with materialThe chloroform solution was then dried over anhydrous sodium sulfate
  5. customevaporated to a syrup
  6. dissolutionThis was dissolved in methanol
  7. additionthe solution, after the addition of 5 ml
  8. temperature1N sodium methylate solution was heated for 10 minutes on a steambath
  9. temperatureAfter cooling
  10. distillationthe solution was distilled off to dryness
  11. dissolutionthe residue was dissolved in chloroform
  12. washthe chloroform solution was washed with water
  13. customThe organic phase was dried
  14. customevaporated
  15. customthe residue obtained
  16. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b7c27c6cbeb44b0c8608986e663e7733
Source dataset
uspto-grants-1977_04
Patent number
US04016262

Linked notes

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