Ethanol → 2-Amino-9-[(2-benzoyloxy-1-(benzoyloxymethyl)ethoxy)methyl]-9H-purine

HRID 64625Notes

Reaction equation

HRID 64625 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH:13]([CH2:24][O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:14][O:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:4](Cl)[N:3]=1.C(O)C.O1CCCC1>[Pd].C(N(CC)CC)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH:13]([CH2:24][O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:14][O:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 8028TetrahydrofuranHCID 13714019HCID 13714019, compound

Product 1

HCID 137140202-Amino-9-[(2-benzoyloxy-1-(benzoyloxymethyl)ethoxy)methyl]-9H-purine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 3.393 g (7.04 mM) of 2-amino-9-[(2-benzoyloxy-1-(benzoyloxymethyl)ethoxy)methyl]-6-chloro-9H-purine, 100 ml ethanol, 100 ml tetrahydrofuran, 1.9 ml triethylamine was added to 0.6 g Pd-C catalyst in a Parr bottle. The mixture was shaken under 50 P.S.I. of H2 for 24 hours. The Pd-C was filtered through a Celite pad and 0.65 g fresh Pd-C was added to the reaction mixture and the hydrogenation was continued for 4 days. Column chromatography using 100% CH2Cl2, 4:1 CH2Cl2 /acetone, and 100% acetone produced the title compound, mpt. 132°-133° C.

Workup

  1. filtrationThe Pd-C was filtered through a Celite pad and 0.65 g fresh Pd-C
  2. additionwas added to the reaction mixture
  3. waitthe hydrogenation was continued for 4 days

Sources & evidence

ORD record
ord-f137d1d6dae04a8eac54c8cf57763666
Source dataset
uspto-grants-1986_09
Patent number
US04609662

Reaction notes

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