Uracil → 5-Chloro-N-((1-(4-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Uracil	HCID 1174	—
Reactant	8-Hydroxyquinoline	HCID 1923	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	5-chloro-N-((1-(4-iodophenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide	HCID 57640693	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	5-Chloro-N-((1-(4-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide	HCID 24989465	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

The mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide (100 mg, 0.23 mmol), uracil (100 mg, 0.90 mmol), CuI (23 mg, 0.12 mmol), 8-hydroxyquinoline (18 mg, 0.12 mmol), potassium carbonate (96 mg, 0.69 mmol) in 2 mL DMSO in a sealed tube was stirred for 15 hrs at 120° C. The title compound was isolated directly from the reaction mixture using reverse phase prep HPLC. MS found for C18H13ClN6O3S (M+H)+ 429.1, 431.1 (Cl pattern).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07696352B2
Source dataset	uspto-grants-2010_04
ORD ID	ord-75dd383b82b54a618088b59b4b05c484
Source note	uspto-grants-2010_04