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. 2006 Sep 30;15(1):227–234. doi: 10.1016/j.bmc.2006.09.066

Scheme 2.

Scheme 2

Reagents and conditions: (a) N3-benzoyl uracil or N-benzoyl thymine, PPh3, DEAD, THF, rt, overnight, 62% for 13, 66% for 14; (b) 1 M NaOMe, MeOH, CH2Cl2, rt, 6 h, 82% for 15, overnight, 94% for 16; (c) 1 M TBAF, THF, rt, 2 h, 97% for 1, 98% for 2; (d) Ac2O, pyridine, rt, overnight; (e) (i) 1,2,4-triazole, POCl3, pyridine, rt, overnight; (ii) 1,4-dioxane, 28% NH4OH, rt, overnight; (iii) NH3, MeOH, rt, overnight.