Journal of Chemistry

Research Article

Modification of Thionucleobases in Ionic Liquids

Table 1

Preparation of thio-substituted nucleobase in various ionic liquids.


Entry	Reactant 1	Reactant 2	Time	Yield (%)	Ionic liquid

1	6-Mercaptopurine	Benzyl bromide	0.5 h	94	[MeOEtMIM]⁺[CF₃COO]⁻
2	6-Mercaptopurine	Benzyl chloride	0.5 h	88^a	[BMIM]⁺[CF₃COO]⁻
3	6-Mercaptopurine	1-Bromopropane	24 h	72^a	[BMIM]⁺[CF₃COO]⁻
4	6-Mercaptopurine	1-Iodobutane	6 h	94	[MeOEtMIM]⁺[CF₃COO]⁻
5	6-Mercaptopurine	1-Iodobutane	6 h	89	[BMIM]⁺[CF₃COO]⁻
6	6-Mercaptopurine	1-Iodobutane	6 h	n	DMSO
7	6-Thioguanine	Benzyl bromide	0.5 h	88	[MeOEtMIM]⁺[CF₃COO]⁻
8	6-Thioguanine	1-Iodobutane	6 h	92	[MeOEtMIM]⁺[CF₃COO]⁻
9	2-Mercaptopyrimidine	Benzyl bromide	0.5 h	93	[BMIM]⁺[CF₃COO]⁻
10	2-Mercaptopyrimidine	1-Bromopropane	24 h	92	[MeOEtMIM]⁺[CF₃COO]⁻
11	2-Mercaptopyrimidine	1-Bromopropane	24 h	92	[PhOEtMIM]⁺[CF₃CF₂COO]⁻
12	2-Mercaptopyrimidine	1-Bromopropane	24 h	83	[BMIM]⁺[CF₃COO]⁻
13	2-Mercaptopyrimidine	1-Bromopropane	24 h	n	DMSO
14	2-Mercaptopyrimidine	1-Iodobutane	6 h	90	[BMIM]⁺[CF₃COO]⁻

Reaction temperature was 60°C. n: no isolated yield of product.