1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → (R)-N-(1-(4-Chlorophenyl)ethyl)-6-(5-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine

Participants

Role	Name	HCID	Charge
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	2-Bromo-5-chloropyridine	HCID 817098	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	(R)-N-(1-(4-Chlorophenyl)ethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine	HCID 58103578	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	(R)-N-(1-(4-Chlorophenyl)ethyl)-6-(5-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine	HCID 25033493	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of (R)-N-(1-(4-chlorophenyl)ethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine (80.0 mg, 0.277 mmol), 2-bromo-5-chloropyridine (69 mg, 0.36 mmol), dry toluene (5 mL), xantphos (10 mg, 0.02 mmol), sodium tert-butoxide (40 mg, 0.42 mmol), and tris(dibenzylideneacetone)dipalladium(0) (6.3 mg, 0.0069 mmol) under N2 was heated in an oil bath at 100° C. for 1.5 h. The mixture was absorbed on silica gel and purified by column (0-5% MeOH/CH2Cl2) to afford a light tan powder.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08653091B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-e5c0af950a1f493bbeebfdc95b1e00fd
Source note	uspto-grants-2014_02