Triethylamine → 3-(9-((5-chloro-2-((1,3-dimethyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)-3-oxopropanenitrile

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Cyanoacetic acid	HCID 9740	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	5-chloro-N2-(1,3-dimethyl-1H-pyrazol-4-yl)-N4-(3-azaspiro[5.5]undecan-9-yl) pyrimidine-2,4-diamine	HCID 118390033	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	3-(9-((5-chloro-2-((1,3-dimethyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)-3-oxopropanenitrile	HCID 118390082	72.8%

Reaction Steps

To a solution of 5-chloro-N2-(1,3-dimethyl-1H-pyrazol-4-yl)-N4-(3-azaspiro[5.5]undecan-9-yl)pyrimidine-2,4-diamine (238.1 mg, 0.6107 mmol) and 2-cyanoacetic acid (132.3 mg, 1555 mmol) in DCM (10 mL) and DMF (3 mL) were added HATU (703.4 mg, 17.94 mmol) and Et3N (225 mg, 2.201 mmol). The mixture was stirred at room temperature for 3 h and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (V/V)=1/5) to give the title compound as a light yellow solid (203.1 mg, 72.8%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09403801B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-16d57d11f46f452eaea33671e72c329e
Source note	uspto-grants-2016_08