Pyridine → HCID 67281958, compound

HRID 1694536Notes

Reaction equation

HRID 1694536 reaction equation
[C:1]([CH2:3][CH2:4][O:5][CH2:6][O:7][C@@H:8]1[C@H:12]([OH:13])[C@@H:11]([CH2:14][OH:15])[O:10][C@H:9]1[N:16]1[CH:23]=[C:22]([CH3:24])[C:20](=[O:21])[NH:19][C:17]1=[O:18])#[N:2].O1CCCC1.N1C=CC=CC=1.[CH3:36][O:37][C:38]1[CH:59]=[CH:58][C:41]([C:42](Cl)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:43]2[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=2)=[CH:40][CH:39]=1>CO>[CH3:50][O:49][C:46]1[CH:45]=[CH:44][C:43]([C:42]([O:15][CH2:14][C@H:11]2[O:10][C@@H:9]([N:16]3[CH:23]=[C:22]([CH3:24])[C:20](=[O:21])[NH:19][C:17]3=[O:18])[C@H:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][C:1]#[N:2])[C@@H:12]2[OH:13])([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[C:41]2[CH:58]=[CH:59][C:38]([O:37][CH3:36])=[CH:39][CH:40]=2)=[CH:48][CH:47]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 67281198HCID 67281198, compound

Product 1

HCID 67281958HCID 67281958, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the 2′-O-(2-cyanoethoxymethyl)-5-methyluridine (20.7 g, 60.6 mmol) obtained in Step 2 was added anhydrous tetrahydrofuran (150 mL), anhydrous pyridine (150 mL), activated Molecular Sieves 4A (50 g), and 4,4′-dimethoxytrityl chloride (22.6 g, 66.7 mmol), and the mixture was stirred overnight at room temperature. After completion of the reaction, methanol (5 mL) was added to the reaction solution and the mixture was stirred for 15 min. The reaction solution was then filtered under aspiration and washed with ethyl acetate, and the filtrate was concentrated. To the residue was added aqueous saturated sodium bicarbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous saturated brine, dried over magnesium sulfate, filtered and concentrated. The residue was subjected to silica gel chromatography to give 5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-cyanoethoxymethyl)-5-methyluridine (35.6 g; yield 91.2%).

Workup

  1. additionwas added to the reaction solution
  2. stirringthe mixture was stirred for 15 min
  3. filtrationThe reaction solution was then filtered under aspiration
  4. washwashed with ethyl acetate
  5. concentrationthe filtrate was concentrated
  6. additionTo the residue was added aqueous saturated sodium bicarbonate solution
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with aqueous saturated brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-76dc0736c34b4c86972f4e09e997cea5
Source dataset
uspto-grants-2012_04
Patent number
US08158774B2

Reaction notes

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