Cesium carbonate → N-(1-(4-((4-(Pyrimidin-5-yloxy)phenyl)ethynyl)phenyl)propan-2-yl)acetamide

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	N,N-Dimethylglycine hydrochloride	HCID 75605	—
Reactant	5-Iodopyrimidine	HCID 1201421	—
Reactant	N-(1-(4-((4-hydroxyphenyl)ethynyl)phenyl)propan-2-yl)acetamide	HCID 66610715	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	N-(1-(4-((4-(Pyrimidin-5-yloxy)phenyl)ethynyl)phenyl)propan-2-yl)acetamide	HCID 66635455	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

28.1 mg (0.14 mmol) 5-iodopyrimidine, 40.0 mg (0.14 mmol) N-(1-(4-((4-hydroxy-phenyl)ethynyl)phenyl)propan-2-yl)acetamide (I76.1), 1.30 mg (0.07 mmol) CuI, 1.9 mg (0.14 mmol) N,N-dimethylglycine hydrochloride and 58.7 mg (0.18 mmol) Cs2CO3 are added to 1 mL dioxane. The reaction mixture is stirred at 90° C. for 2 h then filtered through a plug of silica gel and washed with DMF. The filtrate is purified by HPLC (MeOH/H2O/TFA).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08835472B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-3e1a1fdc1d1546e5b2efb470e5ef9a12
Source note	uspto-grants-2014_09