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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2090427Generated: October 31, 2026

1,4-Dioxane → HCID 59402348, compound

https://huagongshe.com/reaction/2090427

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,4-DioxaneHCID 31275—
ReactantSodium BicarbonateHCID 516892—
Reactant1-(2-Morpholinoethyl)-1H-pyrazole-4-boronic acid pinacol esterHCID 17749924—
Reactant4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amineHCID 59402317—
CatalystHCID 178418397HCID 178418397—
SolventMethanolHCID 887—
SolventWaterHCID 962—
ProductHCID 59402348HCID 5940234860.8%

Reaction Conditions

Temperature90 °C

Reaction Steps

A mixture of 4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine (10 mg, 0.02 mmol; Peak 1, Example 49, Step 7), 4-{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]ethyl}morpholine (8.8 mg, 0.029 mmol), tetrakis(triphenylphosphine)palladium(0) (1.4 mg, 0.0012 mmol), and sodium bicarbonate (6.0 mg, 0.072 mmol) in a solution of 1,4-dioxane (0.2 mL) and water (0.1 mL) in a reaction vial was stirred at 90° C. overnight. After cooling, it was diluted with methanol. After filtration the filtrate was purified with RP-HPLC (pH=10) to afford the desired product (6.3 mg). LCMS (M+H)+: m/z=518.4.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08436008B2
Source datasetuspto-grants-2013_05
ORD IDord-2c9ba917669a43d5937756be5bc96d9f
Source noteuspto-grants-2013_05