Pyridine → Ortho-nitrobenzyl-2'-deoxyadenosine

HRID 611463Notes

Reaction equation

HRID 611463 reaction equation
[N+:1]([C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[CH2:6][C@@:7]1([N:16]2[C:25]3[N:24]=[CH:23][N:22]=[C:20]([NH2:21])[C:19]=3[N:18]=[CH:17]2)[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]1O)([O-:3])=[O:2].N1C=CC=CC=1.C(N(CC)CC)C>O>[N+:1]([C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[CH2:6][C@@:7]1([N:16]2[C:25]3[N:24]=[CH:23][N:22]=[C:20]([NH2:21])[C:19]=3[N:18]=[CH:17]2)[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[CH2:8]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8471TriethylamineHCID 70146783Ortho-nitrobenzyladenosine

Product 1

HCID 66830961Ortho-nitrobenzyl-2'-deoxyadenosineYield 60.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2'-deoxy-N -bis-ortho-nitrobenzyladenosine (200 mg, 0.518 mmol) was added anhydrous pyridine (10 ml) and evaporated to dryness. Pyridine (10 ml) was added followed by 4-4'-dimethoxytrityl chloride (900 mg, 2.3 mmol, 4.5 equiv.) and triethylamine (280 mg, 2.76 mmol, 4.0 equiv.) and stirred at room temperature under an argon atmosphere for 5 hours. Water (0.5 ml) was added and stirred for 20 minutes. The mixture was partitioned between ether and water (20 ml each) and the aqueous phase was re-extracted with ether (20 ml). The extracts were combined and washed with water (20 ml) and dried over anhydrous sodium sulfate, filtered and evaporated. The material was purified by chromatography on silica gel (4 g, using 0.7-2.5% methanol in methylene chloride) to yield 5'-O-DMT- N6 -bis-ortho-nitrobenzyl-2'-deoxyadenosine, (121 mg, 33%).

Workup

  1. customevaporated to dryness
  2. additionPyridine (10 ml) was added
  3. stirringstirred for 20 minutes
  4. customThe mixture was partitioned between ether and water (20 ml each)
  5. extractionthe aqueous phase was re-extracted with ether (20 ml)
  6. washwashed with water (20 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe material was purified by chromatography on silica gel (4 g, using 0.7-2.5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-974859afdf2f44ef96650343e3f4d30a
Source dataset
uspto-grants-1999_12
Patent number
US06001611

Reaction notes

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