Diisopropylethylamine → (+/-)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-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-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanamine	HCID 86689823	—
Solvent	2,4-Dimethyl-3-pentanol	HCID 11752	—
Product	(+/-)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethyl)pyrimidine-2,4-diamine	HCID 86689871	51.6%

Reaction Conditions

Temperature	140 °C

Reaction Steps

A mixture of (±)-1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanamine (referential example 11) (800 mg, 2.54 mmol), 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-pyrimidin-4-amine (500 mg, 2.12 mmol), and DIPEA (820 mg, 6.36 mmol) in 2,4-dimethylpentan-3-ol (10 mL) in a sealed tube under nitrogen was stirred at 140° C. for 18 h. The crude product was purified by preparative HPLC to afford 563 mg (51.7%) of (±)—N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethyl)pyrimidine-2,4-diamine as a yellow solid (563 mg, 51.7%): MS (ESI) m/z: 515.2 [M+1]+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08815877B2
Source dataset	uspto-grants-2014_08
ORD ID	ord-6046fe36c3e04dd99c1e13091fedc076
Source note	uspto-grants-2014_08