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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1966750Generated: October 29, 2026

Sodium Carbonate → HCID 58541944, compound

https://huagongshe.com/reaction/1966750

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant2-Aminopyrimidine-5-boronic acid, pinacol esterHCID 17750212—
ReactantHCID 58542030HCID 58542030—
CatalystHCID 178418397HCID 178418397—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
ProductHCID 58541944HCID 5854194482%

Reaction Conditions

Temperature110 °C

Reaction Steps

To a sealed vial is added 5-bromo-1-tert-butyl-2-[2-(1-methyl-1H-[1,2,4]triazol-3-yl)-phenyl]-1H-benzimidazole (32 mg, 0.078 mmol) in DMF (2 mL), followed by the addition of 2-aminopyrimidine-5-boronic acid pinacol ester (21 mg, 0.095 mmol), tetrakis(triphenylphosphine)palladium(0) (9 mg, 0.008 mmol) and 2M aq. Na2CO3 (0.2 ml, 0.4 mmol). The reaction mixture is heated under Argon at 110° C. for 2 hours. The residue is diluted with EtOAc, washed with brine, dried under anhydrous Na2SO4, filtered and concentrated. The residue is purified by silica gel flash chromatography with 0-3% 7M NH3 in MeOH/CH2Cl2 as the eluent. The product fractions are collected and concentrated to afford the title compound (27 mg, 82%) as an off-white solid. LCMS (ESMS): m/z 425.66 (M++1)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08420655B2
Source datasetuspto-grants-2013_04
ORD IDord-c8122316a6d641bfb375da75a8037316
Source noteuspto-grants-2013_04