Sodium Iodide → HCID 14326895, compound

Temperature

50 °C

Chlorotrimethylsilane (4.11 ml; 32.5 mmol) was introduced by syringe, into a solution of 1.5 g (10.2 mmol) of the 2-methoxy-5-(1-propynyl)pyrimidine and 4.56 g (30.44 mmol) of NaI in 35 ml of anhydrous acetonitrile maintained under an atmosphere of dry nitrogen and removed from light. The mixture was stirred at 50° C. for 21/2 hours with periodic monitoring by tlc. The mixture was cooled in an ice-bath and 3.5 g (8.14 mmol) of the halogenose, 1-(3,5-di-O-(p-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl)-chloride were then added. To this mixture was added 3 ml of 1N trimethylsilyl triflate in 1,2-dichloroethane; the mixture was stirred at 0° C. for 1 hour and then at room temperature for 21/2 hours. The reaction mixture was then diluted with dichloromethane (150 ml) and saturated aqueous bicarbonate (65 ml). The organic extract was subsequently washed with water (60 ml), dried over magnesium sulfate and concentrated to a residue which was subjected to flash chromatography on 80 g of silica gel. The fractions containing the slower moving alpha anomer were pooled and concentrated to a minimum volume with attendant precipitation. The mixture was cooled and filtered; the white product washed with diethyl ether and dried at 50° C. to provide 1.1 g (25.7%) of 1-(3,5-di-O-)p-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl)-5-(1-propynyl)-2-pyrimidinone; mp 176°-178° C.

1. temperaturemaintained under an atmosphere of dry nitrogen
2. customremoved from light
3. temperatureThe mixture was cooled in an ice-bath
4. addition3.5 g (8.14 mmol) of the halogenose, 1-(3,5-di-O-(p-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl)-chloride were then added
5. additionTo this mixture was added 3 ml of 1N trimethylsilyl triflate in 1,2-dichloroethane
6. stirringthe mixture was stirred at 0° C. for 1 hour
7. customat room temperature
8. custom2 hours
9. additionThe reaction mixture was then diluted with dichloromethane (150 ml) and saturated aqueous bicarbonate (65 ml)
10. extractionThe organic extract
11. washwas subsequently washed with water (60 ml)
12. dry with materialdried over magnesium sulfate
13. concentrationconcentrated to a residue which
14. additionThe fractions containing the
15. concentrationconcentrated to a minimum volume with attendant precipitation
16. temperatureThe mixture was cooled
17. filtrationfiltered
18. washthe white product washed with diethyl ether
19. customdried at 50° C.

ORD record

ord-66a2907635344547a529056e3e564bc8

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04895937