Formamide → HCID 54100180, compound

Temperature

140 °C

To 85.8 mg (0.42 mmol) of 1-(2'-(1",2"-dihydroxyethyl) cyclopropyl)uracil, the product of Step B of Example 9, is added 0.44 mL (2.1 mmol) of hexamethyldisilazane and 0.034 mL (0.82 mmol) of formamide and the resultant mixture is heated with stirring in a sealed tube at 140° C. After 85 h, 10 mL of methanol is added to the cooled reaction mixture, the tube resealed and heated to 65° C. After 3 h at 65° C., the cooled reaction mixture is concentrated under reduced pressure. The residue is dissolved in 10 mL of water and the resultant aqueous solution treated with 50 mg of Darco G-60 charcoal, filtered and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel eluted with a gradient of methanol in methylene chloride from 100% methylene chloride to 30% methanol affords the title compound.

1. temperatureheated to 65° C
2. waitAfter 3 h at 65° C.
3. customthe cooled reaction mixture
4. concentrationis concentrated under reduced pressure
5. dissolutionThe residue is dissolved in 10 mL of water
6. additionthe resultant aqueous solution treated with 50 mg of Darco G-60 charcoal
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customPurification of the residue by column chromatography on silica gel
10. washeluted with a gradient of methanol in methylene chloride from 100% methylene chloride to 30% methanol

ORD record

ord-9c3ddb56184b419f9ba2875dfc4cfa58

Source dataset

uspto-grants-1991_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04988703