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Table 6 Synthesis of 5-alkynyl pyrimidine analogues 54-59

From: Heck and Sonogashira couplings in aqueous media – application to unprotected nucleosides and nucleotides

Entry R 1 Starting Material R 2 Product Yield (%)
1 OH 11 54 17a
2 H 53 55 41b
3 OH 11 56 17c
4 H 53 57 42d
5 OH 11 58 42e
6 H 53 59 26f
  1. a[Pd(P(C6H4SO3Na)3)4] (5 mol%), (2 eq), NEt3 (35.9 eq), CuI (0.2 eq), 24 h. b[Pd(P(C6H4SO3Na)3)4] (5 mol%), (2 eq), NEt3 (35.9 eq), CuI (0.2 eq), 17 h. c[Pd(PPh2(3-(NaO3SC6H4))4] (10 mol%), (1.5 eq), NEt3 (5 eq), CuI (0.1 eq), 3d. d[Pd(PPh2(3-(NaO3SC6H4))4] (10 mol%), (1.5 eq), NEt3 (130 eq), CuI (0.1 eq), 12 h. e[Pd(PPh2(3-(NaO3SC6H4))4] (10 mol%), (1.8 eq), NEt3 (130 eq), CuI (0.1 eq), 3d. f[Pd(PPh2(3-(NaO3SC6H4))4] (10 mol%), (1.5 eq), NEt3 (5 eq), CuI (0.1 eq), 12 h.