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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 595840Generated: October 30, 2026

Sodium Carbonate → 5-(2-methyl-3,6-dihydro-2H-pyran-4-yl)pyrazin-2-amine

https://huagongshe.com/reaction/595840

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amineHCID 17998987—
Reactant2-methyl-3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonateHCID 118045496—
CatalystHCID 178418807HCID 178418807—
Solvent1,2-DimethoxyethaneHCID 8071—
Product5-(2-methyl-3,6-dihydro-2H-pyran-4-yl)pyrazin-2-amineHCID 11804539545.4%

Reaction Conditions

Temperature120 °C

Reaction Steps

To a solution of 2-methyl-3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate (0.637 g, 2.88 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amine (0.914 g, 3.74 mmol), and PdCl2(dppf)-CH2Cl2 adduct (0.235 g, 0.288 mmol) in DME (9.82 mL) was added 2M Na2CO3 (3.27 mL). The reaction mixture was heated at microwave synthesizer (120° C., 10 min). Ethyl acetated was added, and washed with sat NaHCO3, and water. Then the desired compound was extracted to 1N HCl aqueous layer, and washed with EtOAc. Basified with 2N NaOH, and the product was extracted to EtOAc layer. EtOAc organic layer was washed with water and dried over Na2SO4. Filtered and concentrated to provide 250 mg of desired compound. LCMS (m/z): 192.2 (MH+), 0.40 min.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09242996B2
Source datasetuspto-grants-2016_01
ORD IDord-e82ed1e6ea9e4fdd8a2f4778c27de53b
Source noteuspto-grants-2016_01