Diisopropylethylamine → N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine	HCID 58169118	—
Reactant	1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine	HCID 86689857	—
Solvent	2,4-Dimethyl-3-pentanol	HCID 11752	—
Product	N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine	HCID 86689876	22.5%

Reaction Conditions

Temperature	135 °C

Reaction Steps

A mixture of 1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine (500 mg, 1.5 mmol), 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (353 mg, 1.5 mmol), and DIPEA (581 mg, 4.5 mmol) in 2,4-dimethylpentan-3-ol (2 mL) was heated at 135° C. for 15 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by reverse phase chromatography to afford 180 mg (21%) of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine as a white solid. MS (ESI): m/z=533.3 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08815877B2
Source dataset	uspto-grants-2014_08
ORD ID	ord-97a4e6d33159487cbfbeb66a42d2b200
Source note	uspto-grants-2014_08