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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 592203Generated: October 30, 2026

1,2-Dimethoxyethane → HCID 58447928, compound

https://huagongshe.com/reaction/592203

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DimethoxyethaneHCID 8071—
ReactantSodium CarbonateHCID 10340—
Reactant2-Methylpyridine-4-boronic acid pinacol esterHCID 16414274—
ReactantHCID 86657955HCID 86657955—
CatalystHCID 178418397HCID 178418397—
SolventEthanolHCID 702—
SolventWaterHCID 962—
ProductHCID 58447928HCID 58447928—

Reaction Conditions

Temperature100 °C

Reaction Steps

To a sealed tube were added N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(5,6-dichloropyridin-3-yl)acetamide 184-5 (65 mg, 0.16 mmol), 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 183-2 (42 mg, 0.19 mmol), Pd(PPh3)4 (9 mg, 0.08 mmol), Na2CO3 (84 mg, 0.79 mmol), DME (0.5 mL), H2O (0.5 mL) and ethanol (0.1 mL). The reaction mixture was stirred at 100° C. overnight. After cooling to room temperature, the solvents were removed by rotary evaporation. The crude product was purified by reverse phase HPLC to give N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(2-(2-methylpyridin-4-yl)pyrimidin-5-yl)acetamide 184. MS m/z 465.2 (M+1); 1H NMR 400 MHz (MeOD) δ 8.52(d, 2H), 8.46(d, 1H), 7.98-7.95(m, 2H), 7.87(d, 1H), 7.53(s, 1H), 7.49-7.46(m, 1 Hz), 7.36(dd, 1H), 3.81(s, 2H), 3.67(t, 2H), 3.62(t, 2H), 3.13(t, 2H), 3.08(t, 2H), 2.56(s, 3H), 2.08(s, 3H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09238646B2
Source datasetuspto-grants-2016_01
ORD IDord-b4e2f2dd20f64e73a6fa9d6fc3307452
Source noteuspto-grants-2016_01