Bromine → 5-Bromo-1-(2-deoxy-5-O-phosphonopentofuranosyl)-4-hydroxypyrimidin-2(1H)-one

HRID 420426Notes

Reaction equation

HRID 420426 reaction equation
[P:1]([O:5][CH2:6][C@H:7]1[O:11][C@@H:10]([N:12]2[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]2=[O:14])[CH2:9][C@@H:8]1[OH:20])([OH:4])([OH:3])=[O:2].[Br:21]Br>N1C=CC=CC=1.C(O)(=O)C>[P:1]([O:5][CH2:6][C@H:7]1[O:11][C@@H:10]([N:12]2[CH:19]=[C:18]([Br:21])[C:16](=[O:17])[NH:15][C:13]2=[O:14])[CH2:9][C@@H:8]1[OH:20])([OH:4])([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 24408BromineHCID 650632'-Deoxyuridylic acid

Product 1

HCID 930365-Bromo-1-(2-deoxy-5-O-phosphonopentofuranosyl)-4-hydroxypyrimidin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1049PyridineSolvent

Procedure

5-Bromo-2′-deoxyuridine-5′-phosphate was prepared as follows: 2′-Deoxyuridine-5′-phosphate (6.2 g) was suspended in a mixture of 60 ml pyridine and 30 ml acetic acid. Bromine (0.84 ml) was added with stirring in an ice water bath and stirring continued for 20 hours at room temperature. The solution was concentrated by vacuum. After redissolution in a minimum of water a crude product was precipitated by addition of ethanol. The crude product was chromatographed on Dowex 50 (H+) and eluted with water. The free acid product was precipitated from the concentrated eluent by addition of ethanol.

Workup

  1. stirringstirring
  2. concentrationThe solution was concentrated by vacuum
  3. customAfter redissolution in a minimum of water a crude product was precipitated by addition of ethanol
  4. customThe crude product was chromatographed on Dowex 50 (H+)
  5. washeluted with water
  6. customThe free acid product was precipitated from the concentrated eluent by addition of ethanol

Sources & evidence

ORD record
ord-b72829d4bccd4beca129d8248f2f6bf1
Source dataset
uspto-grants-2012_01
Patent number
US08097405B1

Reaction notes

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