Pyridine → HCID 10651405, compound

HRID 1827447

Reaction equation

HRID 1827447 reaction equation
[CH2:1]([O:8][C@H:9]1[C:13]([CH2:16][OH:17])([CH2:14][OH:15])[O:12][C@@H:11]([N:18]2[CH:26]=[C:24]([CH3:25])[C:22](=[O:23])[NH:21][C:19]2=[O:20])[C@@H:10]1[OH:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>O1CCCC1>[CH2:1]([O:8][C@H:9]1[C:13]([CH2:14][O:15][S:35]([CH3:34])(=[O:37])=[O:36])([CH2:16][O:17][S:35]([CH3:34])(=[O:37])=[O:36])[O:12][C@@H:11]([N:18]2[CH:26]=[C:24]([CH3:25])[C:22](=[O:23])[NH:21][C:19]2=[O:20])[C@@H:10]1[O:27][S:35]([CH3:34])(=[O:37])=[O:36])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 106910381-(3-O-Benzy-4-hydroxymethyl-beta-D-xylofuranosyl)thymine

Product 1

HCID 10651405HCID 10651405, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of nucleoside 5 (1100 mg, 2.91 mmol) in anhydrous tetrahydrofuran (20 cm3) was added anhydrous pyridine (5 cm3) followed by methanesulfonyl chloride (1.2 ml, 15.5 mmol). The mixture was stirred under a nitrogen atmosphere for 18 h at room temperature. The reaction mixture was evaporated to dryness under reduced pressure and dissolved in ethyl acetate. The organic phase was washed with saturated aqueous solution of sodium hydrogen carbonate (3×10 cm3) and dried (Na2SO4). The organic phase was evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane/methanol (2% methanol, v/v) as elutxnt to afford nucleoside 11 (908 mg, 51%). δC (CDCl3) 163.3, 150.6, 135.6, 134.6, 128.7, 128.3, 112.2, 87.9, 85.0, 83.1, 80.9, 77.2, 76.9, 76.6, 73.3, 66.6, 66.2, 38.6, 37.6, 37.6, 12.2.

Workup

  1. customThe reaction mixture was evaporated to dryness under reduced pressure
  2. dissolutiondissolved in ethyl acetate
  3. washThe organic phase was washed with saturated aqueous solution of sodium hydrogen carbonate (3×10 cm3)
  4. dry with materialdried (Na2SO4)
  5. customThe organic phase was evaporated to dryness under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ebbfd4819d234ad38c59ef9f5a9c20b8
Source dataset
uspto-grants-2006_05
Patent number
US07053207B2

Linked notes

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