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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1484836Generated: October 25, 2026

Sodium Carbonate → 2-(4-(4-(Benzyloxy)pyrimidin-2-yl)phenyl)acetonitrile

https://huagongshe.com/reaction/1484836

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant1,4-DioxaneHCID 31275—
Reactant2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrileHCID 3842922—
Reactant4-(Benzyloxy)-2-chloropyrimidineHCID 15133237—
SolventWaterHCID 962—
Product2-(4-(4-(Benzyloxy)pyrimidin-2-yl)phenyl)acetonitrileHCID 5816914431%

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of 4-(benzyloxy)-2-chloropyrimidine (3.2 g, 14.5 mmol, 1.0 equiv.), 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (4.2 g, 17.4 mmol, 1.2 equiv.), Pd(dippf)Cl2 (1.18 g, 1.45 mmol, 0.1 equiv.), Na2CO3 (6.1 g, 58 mmol, 4.0 equiv.), dioxane (5 ml) and water (1 ml) was added to the filtrate. The reaction mixture was heated to 100° C. for 15 h under nitrogen atmosphere. The residue was purified by silica gel chromatography (CH2Cl2/methanol 500:1 to 200:1) to afford 2-(4-(4-(benzyloxy)pyrimidin-2-yl)phenyl)acetonitrile (1.3 g, 31%) as white solid. The title compound was determination by LC-MS (LC-MS (m/z)=302.1 [M+H]+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09422271B2
Source datasetuspto-grants-2016_08
ORD IDord-e84f68b1f54d49de942bbf9481d80bc8
Source noteuspto-grants-2016_08