Potassium peroxymonosulphate → HCID 58042463, compound

An aqueous solution (5 mL) of potassium peroxymonosulfate (1.40 g, 2.27 mmol) was added dropwise to a solution of 2-isopropoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (Preparation 45, 500 mg, 1.89 mmol) in acetone (5 ml) under a nitrogen atmosphere at 0° C. The mixture was stirred at room temperature for 2 hours, then filtered, the filtrate diluted with water (30 mL) and extracted with EtOAc (1×20 mL). The organic layer was washed with brine (2×20 mL), dried over sodium sulfate, filtered and evaporated in vacuo. The resulting oil was dissolved in DCM and purified by silica gel chromatography eluting with 0 to 5% MeOH (with 10% aqueous ammonia) in DCM to yield a solid. The solid was suspended in diethyl ether and evaporated to yield the title compound as a white solid (100 mg, 34%):

1. filtrationfiltered
2. additionthe filtrate diluted with water (30 mL)
3. extractionextracted with EtOAc (1×20 mL)
4. washThe organic layer was washed with brine (2×20 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customevaporated in vacuo
8. dissolutionThe resulting oil was dissolved in DCM
9. custompurified by silica gel chromatography
10. washeluting with 0 to 5% MeOH (with 10% aqueous ammonia) in DCM
11. customto yield a solid
12. customevaporated

ORD record

ord-4113707924684598a43e5a8a4b0d0b31

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592629B2