Iodine → HCID 10043561, compound

Temperature

21 °C

To a suspension of thymidine (0.968 g, 4.0 mM) in dioxane (20 mL) containing pyridine (0.65 mL, 8.0 mM) was added triphenylphosphine (1.57 g, 6.0 mM) and iodine (1.52 g, 6.0 mM). After stirring the mixture for 7 hours at 21° C., methanol (1.0 mL) was added, followed by removal of the solvent by evaporation. A solution of the residue in ethyl acetate (150 mL) was extracted successively with water (30 mL), 10% aqueous sodium thiosulfate solution (30 mL), and brine (30 mL). The ethyl acetate phase was concentrated in vacuo to a sirup which was taken up in hot ethanol (50 mL) and filtered. The filtrate was concentrated to a volume of 15 mL. On cooling, 5'-deoxy-5'-iodothymidine crystallized out. The crystals were filtered, rinsed with ethyl acetate, and dried, affording 5'-deoxy-5'-iodothymidine (0.806 g), a compound according to Formula 2.

1. customfollowed by removal of the solvent by evaporation
2. extractionA solution of the residue in ethyl acetate (150 mL) was extracted successively with water (30 mL), 10% aqueous sodium thiosulfate solution (30 mL), and brine (30 mL)
3. concentrationThe ethyl acetate phase was concentrated in vacuo to a sirup which
4. filtrationfiltered
5. concentrationThe filtrate was concentrated to a volume of 15 mL
6. temperatureOn cooling
7. custom5'-deoxy-5'-iodothymidine crystallized out
8. filtrationThe crystals were filtered
9. washrinsed with ethyl acetate
10. customdried

ORD record

ord-7e114ca83be04bcf85ef0fd530ecfda7

Source dataset

uspto-grants-1995_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05449664