Trimethylsilyl triflate → 4-Chloro-1-(2-O-methyl-3,5-di-O-benzoyl-beta-D-ribofuranosyl)-pyrimidin-2-one

4-Chloro-2-trimethylsilylethoxy-pyrimidine (3.5 g, 15.2 mmole) and 2-O-methyl-1,3,5-tri-O-benzoyl-α-D-ribose (7.0 g, 15.2 mmole) were dissolved in acetonitrile (100 ml). This solution was treated with trimethylsilyl trifluoromethanesulfonate (2.8 g, 15.2 mmole) and stirred for 1.5 hours. The reaction mixture was concentrated to an oil and redissolved in 300 ml CH2Cl2. The CH2Cl2 solution was washed with cold concentrated sodium bicarbonate, dried over magnesium sulfate, filtered, and evaporated to an oil. The oil was coevaporated with acetonitrile and dried to a brown foam to give 6.70 g (91%) crude product.

1. concentrationThe reaction mixture was concentrated to an oil
2. dissolutionredissolved in 300 ml CH2Cl2
3. washThe CH2Cl2 solution was washed with cold concentrated sodium bicarbonate
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. customevaporated to an oil
7. customdried to a brown foam

ORD record

ord-28f666b72fb4495ba2c9b198afa6f7c7

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05459243