Diisopropylethylamine → tert-butyl 5-((5-cyano-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	3-Amino-1-methylpyrazole hydrochloride	HCID 60150246	—
Reactant	tert-butyl 5-((2-chloro-5-cyanopyrimidin-4-yl)amino)hexahvdrocyclopenta[c]pyrrole-2(1H)-carboxylate	HCID 118390007	—
Solvent	1-Butanol	HCID 263	—
Product	tert-butyl 5-((5-cyano-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate	HCID 118390115	96.56%

Reaction Conditions

Temperature	150 °C

Reaction Steps

To a solution of tert-butyl 5-((2-chloro-5-cyanopyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (377.2 mg, 1.037 mmol) and 1-methylpyrazol-3-amine hydrochloride (277.5 mg, 2.077 mmol) in butan-1-ol (15 mL) was added DIPEA (335.5 mg, 2.596 mmol). The mixture was stirred at 150° C. overnight, then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=50/1) to give the title product as a yellow solid (425 mg, 96.56%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09403801B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-e1ebd6c13fb74b8988a0bd9faf84b98c
Source note	uspto-grants-2016_08