Water → HCID 18665399, compound

Temperature

0 °C

To the phenyl 2,3-dideoxy-1-thio-D-glycero-pentofuranoside (465 mg, 2.21 mmol) was added dimethylformamide (10 ml) under an argon atmosphere and then, sodium hydride (50% oil, 230 mg) having been washed with hexane was added thereto. The resultant mixture was allowed to react at room temperature for 1 hour and cooled to 0° C. To the reaction mixture was added 2-chloro-4-methoxypyridine (519 mg) and a reaction was allowed to proceed for 3 hours. The resultant mixture was gradually heated to room temperature, so that a reaction is further allowed to proceed for 12 hours. After cooling the resultant mixture to 0° C., water and ether were added thereto to thereby extract the organic phase of the mixture with the ether. The thus obtained organic phase was dried over anhydrous magnesium sulfate and concentrated by evaporation of the ether under reduced pressure. The resultant concentrate was subjected to silica gel thin-layer chromatography (developing solvent; ether:hexane=1:2 to 3:1) to thereby obtain 631 mg of phenyl 2,3-dideoxy-5-O-(4-methoxy-2-pyrimidyl)-1-thio-D-glycero-pentofuranoside (yield: 90%). The structure of this compound was confirmed by 1H NMR. The 1H NMR spectrum is shown in FIG. 1, and the 1H NMR data is as follows:

1. washsodium hydride (50% oil, 230 mg) having been washed with hexane
2. additionwas added
3. customto react at room temperature for 1 hour
4. waitto proceed for 12 hours
5. extractionto thereby extract the organic phase of the mixture with the ether
6. dry with materialThe thus obtained organic phase was dried over anhydrous magnesium sulfate
7. concentrationconcentrated by evaporation of the ether under reduced pressure
8. concentrationThe resultant concentrate

ORD record

ord-8ec00269c13041d184bc21247f40dde5

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05811540