反应详情

To a cold (0° C.) solution of benzylated 6-chlorouracil 2 (10 g, 38 mmol) in DMF-TH-F (1:1, 300 mL) under nitrogen, was added NaH (60%, 1.6 g, 39.9 mmol) in portions, followed by adding LiBr (2 g). The mixture was stirred at RT for 20 min. After adding iodomethane (5.4 mL, 76 mmol), the flask was sealed and stirred at this temperature for 10 min, RT for 2 h, and 35° C. overnight, and then concentrated in vacuo. The residue was dissolved in CHCl3 and washed with water and brine, dried (Na2SO4), and filtered then concentrated in vacuo. The crude product was crystallized from THF-Hexanes to give 7.6 g (72%) of the title compound 3. 1H NMR (400 MHz, DMSO): δ 7.87 (d, 1H, J=7.6 Hz), 7.70 (t, 1H, J=7.6 Hz), 7.51 (t, 1H, J=7.6 Hz), 7.40 (d, 1H, J=8 Hz), 6.21 (s, 1H), 5.38 (s, 2H), 3.28 (s, 3H). MS (ES) [m+H] calc'd for C13H11ClN3O2, 276.1; found 276.1.

1. customthe flask was sealed
2. stirringstirred at this temperature for 10 min, RT for 2 h
3. concentration35° C. overnight, and then concentrated in vacuo
4. dissolutionThe residue was dissolved in CHCl3
5. washwashed with water and brine
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationthen concentrated in vacuo
9. customThe crude product was crystallized from THF-Hexanes