2-(Tributylstannyl)pyridine → 5-(4-Chloro-phenyl)-1-phenyl-6-(4-pyridin-2-yl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Participants

Role	Name	HCID	Charge
Reactant	2-(Tributylstannyl)pyridine	HCID 607784	—
Reactant	6-(4-Bromophenyl)-5-(4-chlorophenyl)-1-phenyl-1H,4H,5H-pyrazolo[3,4-D]pyrimidin-4-one	HCID 2047202	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Toluene	HCID 1140	—
Product	5-(4-Chloro-phenyl)-1-phenyl-6-(4-pyridin-2-yl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one	HCID 11518533	46%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A reaction tube charged with 6-(4-bromophenyl)-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (40.0 mg, 0.084 mmol) and Pd(PPh3)4 (9.7 mg, 0.0084 mmol) is purged with nitrogen. A solution of 2-tributylstannanyl-pyridine (61.6 mg, 0.168 mmol) in anhydrous toluene (1.0 mL) is added via syringe. The reaction mixture is heated at 100° C. overnight, and is partitioned between water and ethyl acetate. The organic phase is washed with brine, concentrated, and purified by preparative LCMS followed by silica gel chromatography to provide the title compound (18.4 mg, 46% yield) as a white solid product; HPLC-MS calculated for C28H18ClN5O (M+H+) 476.1. Found: 476.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08158634B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-098150a7c1b2492d9c988ea7b506e1e7
Source note	uspto-grants-2012_04