8-Bromo-2'-deoxyadenosine → 2'-Deoxy-8-methoxyadenosine

HRID 2050604Notes

Reaction equation

HRID 2050604 reaction equation
Br[C:2]1[N:3]([C:12]2[N:13]=[CH:14][N:15]=[C:16]([NH2:19])[C:17]=2[N:18]=1)[C@@H:4]1[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[CH2:5]1.[CH3:20][O-:21].[Na+]>CO>[CH3:20][O:21][C:2]1[N:3]([C:12]2[N:13]=[CH:14][N:15]=[C:16]([NH2:19])[C:17]=2[N:18]=1)[C@@H:4]1[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[CH2:5]1

Participants

4

Reactant 2

HCID 965478-Bromo-2'-deoxyadenosineHCID 10942334Sodium Methoxide

Product 1

HCID 539094342'-Deoxy-8-methoxyadenosineYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8-bromo-2'-deoxyadenosine (1.85 g, 5.61 mmol) in methanol (100 ml) was added sodium methoxide (0.908 g, 16.8 mmol), and the mixture was refluxed for 20 h. The solvent was evaporated and the residue chromatographed on silica gel (5% methanol/chloroform) to give 0.865 g (55%) of 2'-deoxy-8-methoxyadenosine: 1H NMR (Me2SO-d6) δ2.11 (m, 2H), 3.53 (m, 2H), 3.81 (m, 1H), 4.10 (s, 3H), 4.38 (m, 1H), 5.24 (m, 2H), 6.18 (t, 1H, J=6.8 Hz), 6.89 (br.s, 2H), 8.02 (s, 1H); UV (H2O) λmax 261 nm. 2'Deoxy-8-methoxyadenosine was converted to 2',3'-dideoxy-8-methoxydenosine (IX) by using in sequence Procedures A (64%), D (83%), and E and F (79%): mp 197°-799° C.; 13C NMR (Me2SO-d6) δ27.0, 28.9, 57.2, 64.0, 81.1, 83.3, 114.8, 148.8, 150.7, 153.9, 154.3; 1H NMR (Me2SO-d6) δ2.16 (m, 4H), 3.51 (m, 2H), 4.10 (br.s, 4H), 5.01 (m, 1H), 6.08 (m, 1H), 6.85 (br.s, 2H), 8.03 (s, 1H); UV (H2O) λmax 260 nm (ε11040); FAB HRMS obsd (M+ +H) 266.1273, calcd for C11H15N5O3 266.1253.

Workup

  1. temperaturethe mixture was refluxed for 20 h
  2. customThe solvent was evaporated
  3. customthe residue chromatographed on silica gel (5% methanol/chloroform)

Sources & evidence

ORD record
ord-ecc0d45573024d54b4bc0f7b8f92c3d3
Source dataset
uspto-grants-1991_05
Patent number
US05013829

Reaction notes

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