Methanol → 2'-O-{2-[(Dimethylamino)oxy]ethyl}-5-methyluridine

HRID 1274802Notes

Reaction equation

HRID 1274802 reaction equation
F.F.F.[CH3:4][N:5]([CH3:36])[O:6][CH2:7][CH2:8][O:9][C@:10]1(CCN)[C@:14](CCN)([OH:15])[C@@H:13]([CH2:19][OH:20])[O:12][C@@:11]1(CCN)[N:21]1[CH:28]=[C:27]([CH3:29])[C:25](=[O:26])[NH:24][C:22]1=[O:23].C(N(CC)CC)C.[Si](OC[C@H]1O[C@@H](N2C=C(C)C(=O)NC2=O)[C@H](OCCON(C)C)[C@@H]1O)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CO>C1COCC1.C(Cl)Cl>[CH3:4][N:5]([CH3:36])[O:6][CH2:7][CH2:8][O:9][C@@H:10]1[C@H:14]([OH:15])[C@@H:13]([CH2:19][OH:20])[O:12][C@H:11]1[N:21]1[CH:28]=[C:27]([CH3:29])[C:25](=[O:26])[NH:24][C:22]1=[O:23]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 229477015'-O-tert-butyldiphenylsilyl-2'-O-[N,N-dimethylaminooxyethyl)-5-methyluridineHCID 131722203HCID 131722203, compound

Product 1

HCID 229476992'-O-{2-[(Dimethylamino)oxy]ethyl}-5-methyluridineYield 92.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2'-O-(dimethylaminooxyethyl)-5-methyluridine Triethylamine trihydrofluoride (3.91 mL, 24.0 mmol) was dissolved in dry THF and triethylamine (1.67 mL, 12 mmol, dry, kept over KOH). This mixture of triethylamine-2HF was then added to 5'-O-tert-butyldiphenylsilyl-2'-O-[N,N-dimethylaminooxyethyl]-5-methyluridine (1.40 g, 2.4 mmol) and stirred at room temperature for 24 hrs. Reaction was monitored by TLC (5% MeOH in CH2Cl2). Solvent was removed under vacuum and the residue placed on a flash column and eluted with 10% MeOH in CH2Cl2 to get 2'-O-(dimethylaminooxyethyl)-5-methyluridine (766 mg, 92.5%).

Workup

  1. customReaction
  2. customSolvent was removed under vacuum
  3. washeluted with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-23d65351a60943e68a604a3e7244fcaa
Source dataset
uspto-grants-2000_12
Patent number
US06159734

Reaction notes

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