Diisopropylethylamine → N2-(1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)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-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine	HCID 86689850	—
Solvent	2,4-Dimethyl-3-pentanol	HCID 11752	—
Product	N2-(1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine	HCID 86689873	142.2%

Reaction Conditions

Temperature	140 °C

Reaction Steps

A mixture of 1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine (180 mg, 0.51 mmol), DIPEA (133 mg, 1.03 mmol), and 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (97 mg, 0.41 mmol) in 2,4-dimethyl-3-pentanol (0.5 mL) was heated at 140° C. for 18 h. The reaction mixture was concentrated under reduced pressure to afford a crude 320 mg (41%) of N2-(1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine as brown solid, which was used in the next step without further purification. MS (ESI): m/z=549.2 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08815877B2
Source dataset	uspto-grants-2014_08
ORD ID	ord-80085f616b154077b226175715393be9
Source note	uspto-grants-2014_08