Potassium Carbonate → HCID 118364788, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-(4-Methylpiperazine-1-carbonyl)phenylboronic acid pinacol ester	HCID 2760030	—
Reactant	HCID 73507291	HCID 73507291	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 118364788	HCID 118364788	98%

Reaction Conditions

Temperature	80 °C

Reaction Steps

(S)-4-(5-bromopyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine (50 mg, 0.11 mmol), (4-methylpiperazin-1-yl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)methanone (45 mg, 0.13 mmol), Pd(dppf)2Cl2 (4.5 mg, 0.0054 mmol), and K2CO3 (45 mg, 0.33 mmol) were dissolved in dioxane (4 ml)+H2O (1 ml), and then degassed with N2(gas), followed by stirring at 80° C. for 2 hours. After the completion of the reaction, the reaction mixture was extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (MeOH:MC=1:10), to give (S)-(4-(2-(2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholino)pyrimidin-5-yl)phenyl) (4-methylpiperazin-1-yl)methanone (62 mg, 98%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09403831B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-c1fbe3a7972142c3b0d3d4982f3409b0
Source note	uspto-grants-2016_08