1,2,3,4-Tetrahydroquinoline → 2-Chloro-4-(1,2,3,4-tetrahydroquinolin-1-yl)pyrimidine

Participants

Role	Name	HCID	Charge
Reactant	1,2,3,4-Tetrahydroquinoline	HCID 69460	—
Reactant	2,4-Dichloropyrimidine	HCID 77531	—
Reagent	Cesium carbonate	HCID 10796	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	2-Chloro-4-(1,2,3,4-tetrahydroquinolin-1-yl)pyrimidine	HCID 22731923	7.28%

Reaction Conditions

Temperature	120 °C

Reaction Steps

2,4-dichloropyrimidine (200 mg, 1.34 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (78 mg, 0.13 mmol), Tris(dibenzylideneacetone)dipalladium(0) (61.5 mg, 0.07 mmol) and Cesium carbonate (656 mg, 2.01 mmol) was added to a microwave vial. toluene (2 mL) was added. 1,2,3,4-tetrahydroquinoline (179 mg, 1.34 mmol) was added. Heated to 120ºC in microwave oven for 90min. Crude filtered through celite and then added to prepHPLC. 30-70% acetonitrile in water. Pure fractions pooled and then freezedried over night. Yielded 1-(2-chloropyrimidin-4-yl)-1,2,3,4-tetrahydroquinoline (24.00 mg, 7.28 %)

Provenance & Evidence

Source dataset	750 AstraZeneca ELN dataset
ORD ID	ord-4dd72fee5c294abbb8cdefc25f205782
Source note	750 AstraZeneca ELN dataset