Dideoxycytidine → Diisopropylaminomethylene 2',3'-dideoxycytidine

HRID 729053

Reaction equation

HRID 729053 reaction equation
[C@@H:1]1([N:8]2[CH:15]=[CH:14][C:12]([NH2:13])=[N:11][C:9]2=[O:10])[O:7][C@H:4]([CH2:5][OH:6])[CH2:3][CH2:2]1.CO[CH:18](OC)[N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21]>CN(C=O)C>[CH:20]([N:19]([CH:18]=[C:2]1[CH2:3][C@@H:4]([CH2:5][OH:6])[O:7][C@H:1]1[N:8]1[CH:15]=[CH:14][C:12]([NH2:13])=[N:11][C:9]1=[O:10])[CH:23]([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 24066DideoxycytidineHCID 13161384Diisopropylformamide Dimethylacetal (>90%)

Product 1

HCID 131717010Diisopropylaminomethylene 2',3'-dideoxycytidineYield 79.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a typical reaction--previously dried 2',3'-dideoxycytidine (153 mg, 0.724 mmoles) prepared by the literature procedures described above is treated with diisopropylformamide dimethylacetal (1.27 g, 7.24 mmoles) in anhydrous DMF (2 mL) under an argon atmosphere. The contents are stirred overnight and then the solvent and excess reagent are removed by rotary evaporation. The syrupy residue remaining is crystallized from ethanol-ether to give pale lemon-colored crystals (185 mg, 79%) of diisopropylaminomethylene 2',3'-dideoxycytidine.

Workup

  1. customIn a typical reaction
  2. customthe solvent and excess reagent are removed by rotary evaporation
  3. customThe syrupy residue remaining is crystallized from ethanol-ether

Sources & evidence

ORD record
ord-fa786e27cfb34f2f97e82278b77890f2
Source dataset
uspto-grants-1991_09
Patent number
US05051498

Linked notes

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