Thymine → 1-(5-Methoxytetrahydro-2-furyl)thymine

Temperature

145 °C

To a suspension of thymine (2.5 g, 20 mmol) in hexamethyldisilazane (30 mL) was added ammonium sulfate (50 mg) and chlorotrimethylsilane (0.5 mL) and the mixture was heated at 145° C. for 4 hr under nitrogen. The excess hexamethyldisilazane was removed at reduced pressure, and the residual oil was dissolved in xylene and evaporated in vacuo to give a colorless viscous oil. To this silylated thymine in dichloroethane (40 mL) was added 2,5-dimethoxytetrahydrofuran (7 mL). After cooling the solution to -30° C., tin tetrachloride (2.3 mL) was added dropwise via a syringe under nitrogen. The mixture was allowed to warm to -10° C. and was then poured into ice cold aqueous sodium bicarbonate (100 mL) and ethyl acetate (150 mL). The mixture was filtered and the organic phase was separated and dried (MgSO4). The solvent was removed under reduced pressure and the residual oil was chromatographed on silica gel using CH2Cl2 /5% MeOH as eluent to give the title compound as a cis/trans mixture in a ratio of 1:1 as shown by analytical HPLC and 1H-NMR: yield 3.4 g (75%).

1. customThe excess hexamethyldisilazane was removed at reduced pressure
2. dissolutionthe residual oil was dissolved in xylene
3. customevaporated in vacuo
4. customto give a colorless viscous oil
5. temperatureAfter cooling the solution to -30° C.
6. temperatureto warm to -10° C.
7. filtrationThe mixture was filtered
8. customthe organic phase was separated
9. dry with materialdried (MgSO4)
10. customThe solvent was removed under reduced pressure
11. customthe residual oil was chromatographed on silica gel

ORD record

ord-eb7c577d427641d3b098b5304ce0b096

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05726174