Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Thymidine | HCID 5789 | — |
| Reactant | 2-Chloro-N,N-diethyl-1,1,2-trifluoroethan-1-amine | HCID 136184 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2,3'-Anhydrothymidine | HCID 6915752 | 60.3% |
Reaction Steps
Thymidine (85.4 g; 0.353 mol) was dissolved in 500 mL dry DMF (dimethyl formamide) 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 with vigorous stirring. The product precipitated from this solution and was filtered. The ethanol supernatant was refrigerated then filtered to yield a total of 47.75 g (0.213 mol; 60.3%) of 2,3'-anhydrothymidine mp=228°-230° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04724232 |
|---|
| Source dataset | uspto-grants-1988_02 |
|---|
| ORD ID | ord-a74d48ae4860473095f955cf805e25c4 |
|---|
| Source note | uspto-grants-1988_02 |
|---|
