Table 1.
Van Leusen reaction on 5‐formyluracil
|
| ||||||
|---|---|---|---|---|---|---|
| Entry | TOSMiC | Base | Solvent | Scale | Yielda [%] | |
| [equiv.] | (equiv.) | [g] | 2a | 2b | ||
| 1 | 3 | NH3 (6) | MeOH | 0.125 | 40 | – |
| 2 | 1.6 | NH3 (3) | MeOH | 0.125 | 48 | – |
| 3 | 1.6 | NH3 (3) | MeOH | 0.25 | 59 | – |
| 4 | 1.6 | NH3 (3) | MeOH | 0.5 | 66 | – |
| 5 | 1.6 | NH3 (3) | MeOH | 1 | 85 | – |
| 6 | 1.6 | NH4OH (3) | MeOH | 0.25 | 23 | – |
| 7 | 1.6 | NH4OH (3) | H2O | 0.25 | Degb | – |
| 8 | 1.6 | K2CO3 (3) | MeOH | 0.25 | – | m.s.c |
| 9 | 1.6 | tBuOK (3) | MeOH | 0.25 | – | m.s.c |
| 10 | 1.6 | Et3N (3) | MeOH | 0.25 | – | m.s.c |
| 11 | 1.6 | DBU (3) | MeOH | 0.25 | – | n.r.d |
a
Isolated yield.
b
Degradation of starting material.
c
Multiple spots, multiple products (monitored by TLC, MS).
d
No reaction.