Pyridine → HCID 70171879, compound

HRID 2229751Notes

Reaction equation

HRID 2229751 reaction equation
[F:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]1=[O:12].N1C=CC=CC=1.[CH3:24][O:25][C:26]1[C:27]([O:46][CH3:47])=[C:28]([CH:43]=[CH:44][CH:45]=1)[C:29](Cl)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C)C1C=CN=CC=1.CO>[CH3:24][O:25][C:26]1[C:27]([O:46][CH3:47])=[C:28]([CH:43]=[CH:44][CH:45]=1)[C:29]([O:9][CH2:8][C@H:5]1[O:4][C@@H:3]([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[C@H:2]([F:1])[C@@H:6]1[OH:7])([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 1049Pyridine2×HCID 1508512'Fluoro-2'-deoxyuridineHCID 66624882Dimethoxytrityl chloride

Product 1

HCID 70171879HCID 70171879, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Procedure

0.5 g (about 2 mmol) of 2′-fluoro-2′-deoxyuridine is coevaporated with 10 ml of abs. pyridine twice in a 50 ml Schlenk flask. The dried nucleoside is taken up in 25 ml of abs. pyridine and, at room temperature, 0.66 g (about 2.2 mmol) of dimethoxytrityl chloride and 10 mg of 4-dimethylaminopyridine are added. After three hours, 1 ml of methanol was added to the mixture, which was then evaporated to dryness in vacuo. The remaining oil is taken up in 50 ml of methylene chloride (deacidified over aluminum oxide) and extracted three times with 50 ml of water. The organic phase is dried over sodium sulfate. After the methylene chloride had been stripped off, the crude product remained as a solid foam. To remove more highly tritylated components and the tritanol, the crude product was digested with 30 ml of abs. benzene at 40-50° C.

Workup

  1. customwas then evaporated to dryness in vacuo
  2. extractionextracted three times with 50 ml of water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customTo remove more highly tritylated components
  5. customat 40-50° C.

Sources & evidence

ORD record
ord-548b9b1e42234d5c919442274493a37d
Source dataset
uspto-grants-2002_07
Patent number
US06420546B1

Reaction notes

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