Triethylamine → 2-(6-{[(1R,2R)-2-(phenylmethoxy)cyclopentyl]amino}purin-9-yl)(4S,3R,5R)-5-(hydroxymethyl)oxolane-3,4-diol

HRID 916544Notes

Reaction equation

HRID 916544 reaction equation
[CH:1]1[N:6]=[C:5](Cl)[C:4]2[N:8]=[CH:9][N:10]([C@@H:11]3[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]3[OH:19])[C:3]=2[N:2]=1.C(N(CC)CC)C.[CH2:27]([O:34][C@@H:35]1[CH2:39][CH2:38][CH2:37][C@H:36]1[NH2:40])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(O)C>[C:28]1([CH2:27][O:34][C@@H:35]2[CH2:39][CH2:38][CH2:37][C@H:36]2[NH:40][C:5]2[N:6]=[CH:1][N:2]=[C:3]3[C:4]=2[N:8]=[CH:9][N:10]3[CH:11]2[C@H:12]([OH:19])[C@H:13]([OH:18])[C@@H:14]([CH2:16][OH:17])[O:15]2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 11863649(1R,2R)-trans-2-Benzyloxy-cyclopentylamine

Product 1

HCID 671896642-(6-{[(1R,2R)-2-(phenylmethoxy)cyclopentyl]amino}purin-9-yl)(4S,3R,5R)-5-(hydroxymethyl)oxolane-3,4-diol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-chloropurine riboside (10.0 g, 35 mmol) in ethanol (350 mL) was added triethylamine (10.0 mL, 100 mmol) and (1R,2R)-2-(benzyloxy)-cyclopentylamine (5.2 g, 52 mmol). The mixture was refluxed for 24 hours, during which the reaction went from a suspension to a clear solution. The ethanol was removed under reduced pressure, and the residue was partitioned between ethyl acetate and water (100 mL:200 mL). The organic layer was separated and the aqueous layer washed with ethyl acetate (2×75 mL). The combined organic layers were dried (sodium sulfate), and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (150 mL), and product precipitated by addition of hexane, to afford 2-(6-{[(1R,2R)-2-(phenylmethoxy)cyclopentyl]amino}purin-9-yl)(4S,3R,5R)-5-(hydroxymethyl)oxolane-3,4-diol as a white solid, (12.0 grams, 77%).

Workup

  1. temperatureThe mixture was refluxed for 24 hours, during which the reaction
  2. customThe ethanol was removed under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water (100 mL:200 mL)
  4. customThe organic layer was separated
  5. washthe aqueous layer washed with ethyl acetate (2×75 mL)
  6. dry with materialThe combined organic layers were dried (sodium sulfate)
  7. customthe solvent was removed under reduced pressure
  8. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  9. customproduct precipitated by addition of hexane

Sources & evidence

ORD record
ord-22b428c15d624a95a2425431396f634c
Source dataset
uspto-grants-2007_09
Patent number
US07271157B2

Reaction notes

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