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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1257908Generated: November 1, 2026

Sodium Carbonate → 1-[4-(2-Aminopyrimidin-5-yl)phenyl]cyclopropanecarboxylic acid

https://huagongshe.com/reaction/1257908

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant2-Aminopyrimidine-5-boronic acid, pinacol esterHCID 17750212—
ReactantTert-butyl 1-(4-bromophenyl)cyclopropanecarboxylateHCID 66661920—
CatalystHCID 178418397HCID 178418397—
SolventEthanolHCID 702—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
Product1-[4-(2-Aminopyrimidin-5-yl)phenyl]cyclopropanecarboxylic acidHCID 6722402160.3%

Reaction Conditions

Temperature120 °C

Reaction Steps

A solution of sodium carbonate (0.56 g, 0.0052 mol) in water (5.0 mL) was added to a mixture of tert-butyl 1-(4-bromophenyl)cyclopropanecarboxylate (0.78 g, 0.0026 mol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (0.87 g, 0.0039 mol), and tetrakis(triphenylphosphine)palladium (0.2 g, 0.0001 mol) in toluene (10 mL) and ethanol (5 mL). The resulting mixture was heated at 120° C. for 15 min, quenched with water (5 mL), and washed with ether (3×10 mL). The precipitate in the aqueous layer was filtered, washed with water, and dried to afford the desired product (0.40 g, 60%). LCMS: (M+H)=256.1.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08461330B2
Source datasetuspto-grants-2013_06
ORD IDord-fac37ee8fe0041a8a69c64c2b3dc6d4e
Source noteuspto-grants-2013_06