Trifluoroacetic acid → tert-butyl 9-((5-chloro-2-((1-(cyclopropylmethyl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	1-(cyclopropylmethyl)-1H-pyrazol-4-amine	HCID 43560372	—
Reactant	Tert-butyl 3-[(2,5-dichloropyrimidin-4-yl)amino]-9-azaspiro[5.5]undecane-9-carboxylate	HCID 118390013	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	tert-butyl 9-((5-chloro-2-((1-(cyclopropylmethyl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylate	HCID 118390018	88.45%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a solution of tert-butyl 9-[(2,5-dichloropyrimidin-4-yl)amino]-3-azaspiro[5.5]undecane-3-carboxylate (500.5 mg, 1.21 mmol) and 1-(cyclopropylmethyl)-1H-pyrazol-4-amine (330.5 mg, 2.41 mmol) in 1,4-dioxane (50 mL) was added trifluoroacetic acid (686.5 mg, 6.02 mmol). The mixture was stirred at 100° C. overnight and concentrated in vacuo. The residue was purified with a silica gel column chromatography (PE/EtOAc (v/v)=1/1 to DCM/MeOH (v/v)=7/1) to give the product as a light yellow solid (550 mg, 88.45%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09403801B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-a724ccd8a0bb49298fcb8bdd57377a3a
Source note	uspto-grants-2016_08