Optimization of reaction conditionsa.
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Entry | Solvent | Base | Time (h) | Yieldb (%) 2ac |
1 | DMF | K2CO3 | 8 | 58(42) |
2 | DMF | Na2CO3 | 8 | 36(30) |
3 | DMF | NaHCO3 | 8 | 29(8) |
4 | DMF | KOC(CH3)3 | 8 | 52(38) |
5 | DMF | Cs 2 CO 3 | 8 | 89(11) |
6 | NMP | Cs2CO3 | 24 | 70 |
7 | THF | Cs2CO3 | 24 | 61 |
8 | DMSO | Cs2CO3 | 24 | 79 |
9 | can | Cs2CO3 | 24 | 69 |
10 | Dioxane | Cs2CO3 | 48 | — |
11 | DMF | NaH | 8 | 2 |
12 | DMF | Cs2CO3 | 8(80 °C) | 62(38) |
13 | DMF | Cs2CO3 | 8(120 °C) | 57(43) |
Unless mentioned, 4,6-bis(4-methoxyphenyl)-pyrimidin-2(1H)-one (0.16 mmol), base (0.16 mmol), and solvents (5 mL) were used in the reaction; addition of propargyl bromide (0.19 mmol) was done at 0 °C and thereafter stirring at room temperature for 8 h.
Isolated yield.
Yield of 3a is given in parenthesis wherever applicable.