Potassium Carbonate → 3-(1-(4-amino-3-(2-aminopyrimidin-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-one

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(2-Aminopyrimidin-5-yl)boronic acid	HCID 17750211	—
Reactant	3-(1-(4-Amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-one	HCID 118131053	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	3-(1-(4-amino-3-(2-aminopyrimidin-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-one	HCID 118131305	28.9%

Reaction Conditions

Temperature	120 °C

Reaction Steps

3-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-one (Intermediate D2a, 60 mg, 0.118 mmol), K2CO3 (32.6 mg, 0.236 mmol), 2-aminopyrimidin-5-ylboronic acid (32.7 mg, 0.236 mmol) and Pd(dppf)Cl2 (4.31 mg, 5.89 μmol) were reacted in 2 ml of dioxane, purged with argon and heated overnight at 120° C. The reaction was quenched by the addition of 1M HClaqueous (2 ml) and the resulting mixture was straightforward purified via reverse phase chromatography using a Biotage C18 30 g SNAP with a gradient of water and acetonitrile (prior to drying 2 ml of 1M HClaqueous were added) to give the title compound (16.2 mg, 28.9%) as a yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09321776B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-329b2ba414ca41488d63c1b525f4c2c9
Source note	uspto-grants-2016_04