Imidazole → 1-[(2-t-Butyldimethylsilyloxyethoxy)methyl]-5-ethyluracil

To 5.6 g (40 mmol) of 5-ethyluracil suspended in 100 ml of dichloromethane was added 22 ml (88 mmol) of bis-(trimethylsilyl)acetamide under a nitrogen atmosphere at room temperature, and the mixture was stirred for 3 hours. To this was further added gently 3.4 ml (48 mmol) of 1,3-dioxolan and 5.6 ml (48 mmol) of tin tetrachloride. The resulting mixture was then subjected to reflux for 17 hours. The reaction mixture thus obtained was poured into 100 ml of a mixture of methanol and water (1:1) containing 22 g of sodium bicarbonate. After stirring for 2 hours, the resulting mixture was filtered through sellaite and the filtrate was evaporated to dryness. To the residue was added 120 ml of acetonitrile, 12 g (80 mmol) of t-butyldimethylsilyl chloride and 5.4 g (80 mmol) of imidazole under a nitrogen atmosphere at room temperature. After 14 hours of stirring, the resulting reaction mixture was concentrated and subjected to partition using an ethyl acetate-water system, and then the organic layer was evaporated to dryness. The residue was adsorbed on a silica gel column and eluted with chloroform. Thereafter, the eluent was subjected to crystallization from a chloroform-hexane solvent to obtain 6.9 g (52%) of 1-[(2-t-butyldimethylsilyloxyethoxy)methyl]-5-ethyluracil.

1. temperatureto reflux for 17 hours
2. customThe reaction mixture thus obtained
3. stirringAfter stirring for 2 hours
4. filtrationthe resulting mixture was filtered through sellaite
5. customthe filtrate was evaporated to dryness
6. stirringAfter 14 hours of stirring
7. customthe resulting reaction mixture
8. concentrationwas concentrated
9. customto partition
10. customthe organic layer was evaporated to dryness
11. washeluted with chloroform
12. customThereafter, the eluent was subjected to crystallization from a chloroform-hexane solvent

ORD 기록

ord-22f07760c82a470c8d4a12a02c6373a5

출처 데이터셋

uspto-grants-1994_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05318972