Diisopropylethylamine → 2-(6-((5-chloro-2-((l-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl)isoindoline-1,3-dione

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1-methyl-1H-pyrazol-4-amine	HCID 17354268	—
Reactant	2-(6-((2,5-Dichloropyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl) isoindoline-1,3-dione	HCID 118387963	—
Solvent	1-Butanol	HCID 263	—
Product	2-(6-((5-chloro-2-((l-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl)isoindoline-1,3-dione	HCID 118387960	33.1%

Reaction Conditions

Temperature	150 °C

Reaction Steps

To a solution of 2-(6-((2,5-dichloropyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl) isoindoline-1,3-dione (370.0 mg, 0.88 mmol) and 1-methyl-1H-pyrazol-4-amine hydrochloride (354.2 mg, 2.65 mmol) in n-BuOH (10 mL) was added DIPEA (683.1 mg, 5.29 mmol). The mixture was stirred at 150° C. overnight. The mixture was concentrated in vacuo, and the residue was purified by silica gel column chromatography (MeOH/CH2C12 (v/v)=1/30) to give the title compound as a red solid (140.0 mg, 33.1%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09394281B2
Source dataset	uspto-grants-2016_07
ORD ID	ord-011255ade86445b29bd87cb8aa169f85
Source note	uspto-grants-2016_07