Trityl chloride → 2'-Deoxy-5'-O-(triphenylmethyl)uridine

HRID 1818663Notes

Reaction equation

HRID 1818663 reaction equation
[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[C:17]1([C:23](Cl)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[C:23]([O:7][CH2:6][C@H:5]1[O:8][C@@H:1]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:2][C@@H:3]1[OH:4])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 13712Deoxyuridine

Product 1

HCID 137119602'-Deoxy-5'-O-(triphenylmethyl)uridineYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2′-Deoxyuridine (1.00 g, 4.39 mmol) and triphenylmethylchloride (1.34 g, 4.83 mmol) were stirred in dry pyridine (20 ml) overnight at 50° C. under an atmosphere of nitrogen. The reaction mixture was then poured into ice-H2O (100 ml) with vigorous stirring and filtered. The precipitate was dissolved in EtOAc (100 ml) and the solution was washed with 0.5M HCl (100 ml) and H2O (100 ml), dried (Na2SO4) and reduced in vacuo. The residue was washed with toluene to leave the title compound (1.99 g, 97%) as a pale yellow solid. For analytical purposes, the compound was purified by gradient flash column chromatography, eluting with 5→10% MeOH/CHCl3.

Workup

  1. filtrationfiltered
  2. dissolutionThe precipitate was dissolved in EtOAc (100 ml)
  3. washthe solution was washed with 0.5M HCl (100 ml) and H2O (100 ml)
  4. dry with materialdried (Na2SO4)
  5. washThe residue was washed with toluene

Sources & evidence

ORD record
ord-c0a019b4f012409f8fdb24876f1d5422
Source dataset
uspto-grants-2009_10
Patent number
US07601702B2

Reaction notes

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