Dimethylformamide dimethyl acetal → N4-Dimethylaminomethylene-2',3'-dideoxy-3'-fluorocytidine

HRID 729054Notes

Reaction equation

HRID 729054 reaction equation
[F:1][C@@H:2]1[C@@H:6]([CH2:7][OH:8])[O:5][C@@H:4]([N:9]2[CH:16]=[CH:15][C:13]([NH2:14])=[N:12][C:10]2=[O:11])[CH2:3]1.CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>CN(C=O)C>[CH3:19][N:20]([CH:22]=[N:14][C:13]1[CH:15]=[CH:16][N:9]([C@@H:4]2[O:5][C@H:6]([CH2:7][OH:8])[C@@H:2]([F:1])[CH2:3]2)[C:10](=[O:11])[N:12]=1)[CH3:21]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 451363Cytidine, 2',3'-dideoxy-3'-fluoro-

Product 1

HCID 451420N4-Dimethylaminomethylene-2',3'-dideoxy-3'-fluorocytidineYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Previously dried 2',3'-dideoxy-3'-fluorocytidine (300 mg, 1.3 mmoles) was treated with dimethylformamide dimethylacetal (0.45 g, 3.8 mmoles) in anhydrous DMF (5 mL) under a nitrogen atmosphere. The contents were stirred overnight and the solvents removed by rotary evaporation. The syrupy residue remaining was crystallized from ethanol to give white crystals (276 mg, 75%) of the product N4 -dimethylaminomethylene-2',3'-dideoxy-3'-fluorocytidine which were shown to have the following properties:

Workup

  1. customthe solvents removed by rotary evaporation
  2. customThe syrupy residue remaining was crystallized from ethanol

Sources & evidence

ORD record
ord-ebabd78a0e644b38934fb6a6f70e2158
Source dataset
uspto-grants-1991_09
Patent number
US05051498

Reaction notes

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