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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1966769Generated: October 31, 2026

Sodium Carbonate → HCID 53237379, compound

https://huagongshe.com/reaction/1966769

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant2-Aminopyrimidine-5-boronic acid, pinacol esterHCID 17750212—
ReactantHCID 58542052HCID 58542052—
CatalystHCID 178418397HCID 178418397—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
ProductHCID 53237379HCID 5323737976%

Reaction Conditions

Temperature110 °C

Reaction Steps

To a sealed vial is added 5-bromo-1-tert-butyl-2-[2-(1,5-dimethyl-1H-[1,2,4]triazol-3-yl)-phenyl]-1H-benzimidazole (38 mg, 0.09 mmol) in DMF (2 mL), followed by the addition of 2-aminopyrimidine-5-boronic acid pinacol ester (24 mg, 0.109 mmol), tetrakis(triphenylphosphine)palladium(0) (11 mg, 0.01 mmol) and 2 M aqueous Na2CO3 (0.2 mL, 0.4 mmol). The reaction mixture is heated under Argon at 110° C. for 3 hours. The residue is diluted with EtOAc (20 mL), washed with brine, dried under anhydrous Na2SO4, filtered and concentrated. The residue is purified by silica gel flash column chromatography with 0-10% MeOH/CH2Cl2 as the eluent to afford the title compound (30 mg, 76%) as an off-white solid. LCMS (ESMS): m/z 439.72 (M++1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08420655B2
Source datasetuspto-grants-2013_04
ORD IDord-881a71b8660d437bb0cce4b43547ba8a
Source noteuspto-grants-2013_04