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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1366123Generated: November 3, 2026

Sodium t-butoxide → (4-(4-Methylpiperazin-1-yl)phenyl)-[5-(2-ethoxypyridin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]amine

https://huagongshe.com/reaction/1366123

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium t-butoxideHCID 23676156—
Reactant2-Ethoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 45786007—
Reactant(5-Bromoimidazo[1,2-a]pyrazin-8-yl)-(4-(4-methylpiperazin-1-yl)phenyl)amineHCID 59022979—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product(4-(4-Methylpiperazin-1-yl)phenyl)-[5-(2-ethoxypyridin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]amineHCID 59023089—

Reaction Conditions

Temperature85 °C

Reaction Steps

A mixture of 2-ethoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine (97 mg, 0.31 mmol), (5-bromoimidazo[1,2-a]pyrazin-8-yl)-(4-(4-methylpiperazin-1-yl)phenyl)amine (100 mg, 0.259 mmol), Pd(PPh3)4 (29 mg, 0.026 mmol) and NaOtBu (99 mg, 1.0 mmol) in DMF (3 mL) and water (1 mL) is heated at 85° C. for 18 hours. After this time the reaction mixture is cooled to room temperature and the solvents removed in vacuo. The residue is chromatographed on silica gel, eluting with DCM followed by 96:4 DCM:NH3 (7M in MeOH), and the fractions containing the desired product are combined and evaporated to afford the title ethoxypyridine as a solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07893058B2
Source datasetuspto-grants-2011_02
ORD IDord-31bc3b28986b4f39ace0de0c21d7014d
Source noteuspto-grants-2011_02