Triethylamine → N(6)-methyl-N(6)-but-2-enyl-adenosine

HRID 328194Notes

Reaction equation

HRID 328194 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.[CH3:29][NH:30][CH2:31][CH:32]=[CH:33][CH3:34].C(N(CC)CC)C>C(O)(C)C>[CH3:29][N:30]([CH2:31][CH:32]=[CH:33][CH3:34])[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]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53970299Methyl-but-2-enylamineHCID 131710375Triacetyl-6-chloro-9-(beta-D-ribofuranosyl)-purine

Product 1

HCID 54015847N(6)-methyl-N(6)-but-2-enyl-adenosineYield 70%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

7.3 g. triacetyl-6-chloro-9-(β-D-ribofuranosyl)-purine, 2.1 g. methyl-but-2-enylamine and 2.8 ml. triethylamine were heated under reflux for 2 hours in 100 ml. isopropanol. After cooling, the reaction mixture was mixed with 200 ml. diethyl ether, extracted twice with water and the organic phase evaporated to dryness in a vacuum. The residue was dissolved in 100 ml. 25% methanolic ammonia and then left to stand overnight at ambient temperature. The solution was thereafter evaporated and the residue obtained was recrystallized from water. 4.1 g. (70% of theory) N(6)-methyl-N(6)-but-2-enyl-adenosine were obtained; m.p. 160° - 162° C.

Workup

  1. temperatureunder reflux for 2 hours in 100 ml
  2. temperatureAfter cooling
  3. additionthe reaction mixture was mixed with 200 ml
  4. extractiondiethyl ether, extracted twice with water
  5. customthe organic phase evaporated to dryness in a vacuum
  6. dissolutionThe residue was dissolved in 100 ml
  7. wait25% methanolic ammonia and then left
  8. customThe solution was thereafter evaporated
  9. customthe residue obtained
  10. customwas recrystallized from water

Sources & evidence

ORD record
ord-23e71be60a3c4d52aa305eab88aec069
Source dataset
uspto-grants-1977_04
Patent number
US04016262

Reaction notes

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