1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → [5-(4-Methoxy-phenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

https://huagongshe.com/reaction/1971609

Participants

Role	Name	HCID	Charge
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	1-(2-(3-Bromophenoxy)Ethyl)-1H-Imidazole	HCID 803108	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	5-(4-Methoxy-phenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-2-ylamine	HCID 59590043	—
Catalyst	Dimethylacetamide	HCID 31374	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	[5-(4-Methoxy-phenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine	HCID 59589626	—

Reaction Conditions

Temperature	150 °C

Reaction Steps

In a microwave vial, 5-(4-methoxy-phenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-2-ylamine (0.05 g, 0.207 mmol), 1-[2-(3-bromo-phenoxy)-ethyl]-1H-imidazole (0.073 g, 0.27 mmol), bis(dibenzylideneacetone)palladium (0.01 g, 0.01 mmol), xantphos (0.012 g, 0.02 mmol) and sodium tert butoxide (0.04 g, 0.416 mmol) were added successively. 1,4-Dioxane (1.2 mL) and dimethylacetamide (4 drops) were added and the vial was sealed and heated in the microwave (150° C., 10 min). The mixture was filtered and purified by preparatory LCMS. LCMS method: 1, RT: 3.27 min; MI: 431 [M+1].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08431596B2
Source dataset	uspto-grants-2013_04
ORD ID	ord-3bf3bc389d794ffba6602650b5ae4120
Source note	uspto-grants-2013_04