Cesium carbonate → 6-(4-Methoxybenzyl)-9-(piperazin-1-ylmethyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5 (6H)-one

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	Potassium (4-tert-butoxycarbonylpiperazin-1-yl)methyltrifluoroborate	HCID 45588144	—
Reactant	9-bromo-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one	HCID 86705385	—
Reactant	tert-Butyl 4-((6-(4-methoxybenzyl)-5-oxo-5,6-dihydropyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-9-yl)methyl)piperazine-1-carboxylate	HCID 131735013	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	1,4-Dioxane--water (1/1)	HCID 21886435	—
Product	6-(4-Methoxybenzyl)-9-(piperazin-1-ylmethyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5 (6H)-one	HCID 118135082	29%

Reaction Conditions

Temperature	80 °C

Reaction Steps

tert-Butyl 4-((6-(4-methoxybenzyl)-5-oxo-5,6-dihydropyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-9-yl)methyl)piperazine-1-carboxylate. 9-Bromo-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 1, 562.00 mg; 1.46 mmol), potassium ((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)trifluoroborate (568.00 mg; 1.86 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (60.00 mg; 0.13 mmol;), Pd(OAc)2 (30.00 mg; 0.13 mmol), Cs2CO3 (1.76 g; 5.40 mmol), and degassed dioxane-water (9:1; 10 mL) were combined in that order and heated at 80° C. for 4 days. The mixture concentrated under reduced pressure. Purification (FCC, SiO2, 20-100% EtOAc/hexanes) afforded the title compound (216 mg, 29%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09284335B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-ef88f57f16f348e2896c15c93dcd5e3b
Source note	uspto-grants-2016_03