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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2090394Generated: November 1, 2026

Nitrogen → HCID 59402355, compound

https://huagongshe.com/reaction/2090394

Reaction equation

Participants

RoleNameHCIDCharge
ReactantNitrogenHCID 947—
ReactantSodium CarbonateHCID 10340—
Reactant1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 2760077—
Reactant4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amineHCID 59402317—
CatalystHCID 178482906HCID 178482906—
SolventWaterHCID 962—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 59402355HCID 59402355—

Reaction Conditions

Temperature90 °C

Reaction Steps

A mixture of 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (11.5 mg, 0.0518 mmol), 4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine (0.018 g, 0.043 mmol) (Peak 1, Example 49, Step 7), dichloro(bis{di-tert-butyl[4-(dimethylamino)phenyl]phosphoranyl})palladium (0.916 mg, 0.00129 mmol), and sodium carbonate (9.14 mg, 0.0862 mmol) in 1,4-dioxane (0.50 mL) and water (0.10 mL) was vacuumed and refilled with N2 for 3 times and then stirred at 90° C. overnight. The mixture was purified by RP-HPLC (pH=10) to afford the desired product. LCMS (M+H)+: m/z=419.3.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08436008B2
Source datasetuspto-grants-2013_05
ORD IDord-744b5b395ea14806b18eba0c78594a22
Source noteuspto-grants-2013_05