Ethanol → 2,3'-Anhydrothymidine

HRID 2248849Notes

Reaction equation

HRID 2248849 reaction equation
[C@@H:1]1([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3](O)[CH2:2]1.ClC(F)C(N(CC)CC)(F)F.C(O)C>CN(C=O)C>[CH3:16][C:15]1[C:13](=[O:14])[N:12]=[C:10]2[N:9]([C@@H:1]3[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([O:11]2)[CH2:2]3)[CH:17]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 5789ThymidineHCID 1361842-Chloro-N,N-diethyl-1,1,2-trifluoroethan-1-amine

Product 1

HCID 69157522,3'-Anhydrothymidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Thymidine (85.4 g: 0.353 mol) was dissolved in 500 mL dry DMF and added to N-(2-chloro-1,1,2-trifluoroethyl)diethylamine (100.3 g; 0.529 mol) (prepared according to the method of D.E. Ayer, J. Med. Chem. 6, 608 (1963)). This solution was heated at 70° C. for 30 minutes then poured into 950 mL ethanol (EtOH) with vigorous stirring. The product precipitated from this solution and was filtered. The EtOH supernatant was refrigerated then filtered to yield the title compound. mp. =230° C.

Workup

  1. customprepared
  2. customThe product precipitated from this solution
  3. filtrationwas filtered
  4. filtrationThe EtOH supernatant was refrigerated then filtered

Sources & evidence

ORD record
ord-255f2565a4504c9fa85d512a21cba499
Source dataset
uspto-grants-1991_08
Patent number
US05041543

Reaction notes

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