Methyl iodide → HCID 88507215, compound

Participants

Reaction Steps

To NaH (5 mmol, 240 mg, 50% in oil, pentane washed and decanted), in DMF (7 mL) was added at -15° C. 6-[1-[1-[bis(4-fluorophenyl)methyl]piperazin-4-yl]-2-hydroxy-3-propanylthio]purine (5 mol, 2.48 g) in DMF (15 mL) over 5 min. After stirring 1 h, methyl iodide (5 mmol, 0.32 mL) in one portion was added at 0° C. under nitrogen. After one hour, the reaction mixture was concentrated under reduced pressure (1 mm Hg, 60° C.) and the crude solid passed through silica gel using 15% MeOH: CH2Cl2 to give the desired product contaminated with DMF. The product was dissolved in CH2Cl2 (50 mL) and washed with H2O (2×50 mL), saturated brine (1×50 mL), dried over Na2SO4 and conconcentrated in vacuo to give pure product (490 mg, 19.2%) as a white glass. mp 68°-70° C. DCI/MS (M+1)=511. (300 MHz) 1H NMR (CDCl3) δ: 8.7 (s, 1H), 7.95 (s, 1H), 7.3 (m, 4H), 6.95 (m, 4H), 4.2 (s, 1H), 4.1 (m, 1H), 3.85 (s, 3H), 3.55 (octet, 2H), 2.6 (m, 2H), 2.6 (m, 4H), 2.35 (m, 4H).

Provenance & Evidence