9-{[1(R)-acetoxymethyl-2(S)-cyclohex-4-enyl]methyl}2-amino-6-benzyloxypurine → HCID 136395916, compound

HRID 1376481Notes

Reaction equation

HRID 1376481 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]1[CH2:11][CH:10]=[CH:9][CH2:8][C@@H:7]1[CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][C:16]([NH2:30])=[N:17][C:18]=2[O:22]CC1C=CC=CC=1)(=[O:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:4][CH2:5][C@@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]1[CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:18](=[O:22])[NH:17][C:16]([NH2:30])=[N:15][C:14]1=2)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 228763119-{[1(R)-acetoxymethyl-2(S)-cyclohex-4-enyl]methyl}2-amino-6-benzyloxypurine

Product 1

HCID 136395916HCID 136395916, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 9-{[1(R)-acetoxymethyl-2(S)-cyclohex-4-enyl]methyl}2-amino-6-benzyloxypurine (0.75 mmol), ethanol (5 mL) and a catalytic amount of 10% Pd/C was stirred under a hydrogen balloon for 3 hours. The reaction was filtered and concentrated to yield the desired compound. 1HNMR (500 mHz, d6DMSO): 10.80 ppm (bs, 1H); 7.65 (s, 1H); 6.48 (s, 2H); 4.15-3.88 (m, 4H); 2.23 (bs, 1H); 2.01 (s, 3H); 1.92 (m, 1H); 1.68-1.15 (m, 8H).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-fd5cce2027e64bb5b30f8db5d32b6e3a
Source dataset
uspto-grants-1997_09
Patent number
US05663175

Reaction notes

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