Effect of a solvent on the synthesis of 6-phenoxypyrimidinea.
| ||||
|---|---|---|---|---|
| Entry | Base | Solvent | Time | Yieldb [%] |
| 1 | NaOH | DMF | 3 h | 76 |
| 2 | DMSO | 72 | ||
| 3 | MeOH | 6 h | 60 | |
| 4 | H2O | 1 h | 81 | |
| 5 | KOH | DMF | 2 h | 78 |
| 6 | DMSO | 74 | ||
| 7 | MeOH | 6 h | 61 | |
| 8 | H2O | 1 h | 84 | |
| 9 | KOH | H2O | 1 h | 78c |
| 10 | KOH | H2O | 1 h | 85d |
| 11 | KOH | H2O | 18 h | 60e |
| 12 | KOH | H2O | 8 h | 80f |
| 13 | KOH | H2O | 1 h | 86 g |
| 14 | KOH | H2O | 1 h | 86 h |
Reaction conditions: 1a (1 mmol), 2a (1.2 mmol), Cu-polymer (10 wt%), base (3 eq.), solvent (3 mL), 100 °C (silicon oil bath).
Isolated yield.
KOH (2 eq.).
KOH (3.5 eq.).
rt.
60 °C.
80 °C.
2a (1.1 mmol), (80 °C).