Cyclopentylamine → HCID 15051904, compound

HRID 636323Notes

Reaction equation

HRID 636323 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:12]1[O:13][CH3:14].[CH:21]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C>C(O)C>[CH:21]1([NH:26][C:2]2[C:3]3[N:4]=[CH:5][N:6]([C:7]=3[N:8]=[CH:9][N:10]=2)[C@@H:11]2[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:12]2[O:13][CH3:14])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 15682117HCID 15682117, compound

Product 1

HCID 15051904HCID 15051904, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1.5 g of 6-chloro-9-(2′-O-methyl-β-D-ribofuranosyl)-9H-purine and 510 mg of cyclopentylamine, 1.5 ml of triethylamine and 70 ml of ethanol were added. The solution was refluxed with heating for several ten minutes to 8 hours. After washing the residue with water, methanol was added and the solution was concentrated to dryness again. The residue was recrystallized with ethyl acetate to give N6-cyclopentyl-2′-O-methyladenosine (Compound 1). yield: 80%

Workup

  1. temperatureThe solution was refluxed
  2. temperaturewith heating for several ten minutes to 8 hours
  3. washAfter washing the residue with water, methanol
  4. additionwas added
  5. concentrationthe solution was concentrated to dryness again
  6. customThe residue was recrystallized with ethyl acetate

Sources & evidence

ORD record
ord-c52f6b98aaed45728580befb05b9855f
Source dataset
uspto-grants-2001_02
Patent number
USRE037077E1

Reaction notes

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