Table 6 Synthesis of 5-alkynyl pyrimidine analogues 54-59
| |||||
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 | |
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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.
(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.