Methyl iodide → HCID 49867280, compound

Adenosine-5′-monophosphate sodium salt (10 g, 24.7 mmol) was dissolved in water (50 mL). The resulting solution was applied to a Dowex 50WX8 column (200 mL) in the pyridinium form. Subsequently the column was washed with 600 mL water-methanol (1:1). The eluate was directly collected into a cold, stirred solution of tri-n-butylamine (17.6 mL, 74.1 mmol) in methanol. The solvent was evaporated to dryness, dissolved again in methanol and re-evaporated twice. This procedure was repeated twice more with anhydrous DMF (700 mL) using an oil pump. The residue was dissolved in 700 mL anhydrous DMF. Iodomethane (50 mL, 803 mmol) was then added and the reaction mixture was stirred at room temperature for 20 hours. The solution was evaporated to dryness. The residue was dissolved in water (1000 mL) and the pH of the solution was adjusted from 1.2 to 7.5 with 1M triethylammonium bicarbonate (pH 11.0). Purification by ion exchange chromatography yielded the product (2.1 g, 23%) as a sodium salt, and was used in the next steps without further purification: MS (ES) m/z 362 [M+H]+, 360 [M+Na]+.

1. washSubsequently the column was washed with 600 mL water-methanol (1:1)
2. customThe eluate was directly collected into a cold
3. customThe solvent was evaporated to dryness
4. dissolutiondissolved again in methanol
5. customre-evaporated twice
6. dissolutionThe residue was dissolved in 700 mL anhydrous DMF
7. customThe solution was evaporated to dryness
8. dissolutionThe residue was dissolved in water (1000 mL)
9. customPurification by ion exchange chromatography

ORD record

ord-56315522d40246ba8115850f5fb12ca0

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569259B2