Skip to main content
. 2023 Jun 5;13(25):16899–16906. doi: 10.1039/d3ra00773a

Optimization of reaction conditionsa.

graphic file with name d3ra00773a-u1.jpg
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)
a

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.

b

Isolated yield.

c

Yield of 3a is given in parenthesis wherever applicable.