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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1478035Generated: October 29, 2026

Triethylamine → 6-(9-((5-chloro-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)nicotinonitrile

https://huagongshe.com/reaction/1478035

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant6-Chloro-3-pyridinecarbonitrileHCID 5152094—
Reactant5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(3-azaspiro[5.5]undecan-9-yl) pyrimidine-2,4-diamineHCID 118390069—
SolventMethanolHCID 887—
SolventDichloromethaneHCID 6344—
Product6-(9-((5-chloro-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)nicotinonitrileHCID 11839002539.7%

Reaction Steps

To a suspension of 5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(3-azaspiro[5.5]undecan-9-yl) pyrimidine-2,4-diamine (0.11 g, 0.29 mmol) in a mixture of DCM and MeOH (5.0 mL/5.0 mL) were added 6-chloropyridine-3-carbonitrile (0.086 g, 0.62 mmol) and Et3N (0.10 mL, 0.72 mmol). The mixture was heated to reflux overnight and then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=50/1) to afford the product as a light yellow solid (55 mg, 39%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09403801B2
Source datasetuspto-grants-2016_08
ORD IDord-4088088784e24c08a01e50de2a7afb52
Source noteuspto-grants-2016_08