Cytidine → Deoxycytidine

HRID 1589897Notes

Reaction equation

HRID 1589897 reaction equation
C(Br)(=O)C.[C@@H:5]1([N:14]2[CH:21]=[CH:20][C:18]([NH2:19])=[N:17][C:15]2=[O:16])[O:13][C@H:10]([CH2:11][OH:12])[C@@H:8]([OH:9])[C@H:6]1O>CC#N.Br.C(O)(=O)C>[C@@H:5]1([N:14]2[CH:21]=[CH:20][C:18]([NH2:19])=[N:17][C:15]2=[O:16])[O:13][C@H:10]([CH2:11][OH:12])[C@@H:8]([OH:9])[CH2:6]1

Participants

6

Reactant 2

HCID 6175CytidineHCID 10482Acetyl bromide

Product 1

HCID 13711DeoxycytidineYield 96.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 260Hydrogen BromideSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Acetyl bromide (16.5 g, 134 mmol, 3.3 eq.) was added dropwise over 0.5 hours to a suspension of cytidine (10 g, 41.1 mmol) in CH3CN (250 mL) and HBr in acetic acid (10 mL, 30% weight) heated at 60°-65° C. The mixture was stirred at 100° C. for 3 hours, and then 10 mL more HBr in acetic acid was added. The mixture was stirred at 100° C. for an additional 28 hours. The solution was removed under vacuum to get a solid, which was purified with silica gel chromatography, to get 9.05 g of a solid (yield 56%).

Workup

  1. temperatureheated at 60°-65° C
  2. stirringThe mixture was stirred at 100° C. for an additional 28 hours
  3. customThe solution was removed under vacuum
  4. customto get a solid, which
  5. customwas purified with silica gel chromatography

Sources & evidence

ORD record
ord-6c95376362214eb68599b49f70ecbfa8
Source dataset
uspto-grants-1993_04
Patent number
US05200514

Reaction notes

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