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methyl 3,5-diamino-6-(furan-3-yl)pyrazine-2-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
85%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In methanol; toluene;Inert atmosphere; Reflux;
General procedure: <strong>[1458-01-1]Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate</strong> 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit.
2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan[ No CAS ]
2,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
31%Spectr.; 11%Spectr.; 5%Spectr.; 5%Spectr.
With Fe(1,2-bis(dimethylphosphino)ethane)2Cl2; sodium 2-ethylhexanoic acid; In tetrahydrofuran; at 60℃; for 48h;Inert atmosphere; Schlenk technique; Irradiation; Glovebox;
General procedure: In an argon-filled glovebox, dmpe2FeCl2 1 (8.6 mg, 0.02 mmol), sodium 2-ethylhexanoate (6.6 mg,0.04 mmol), HBpin (87 L, 0.6 mmol), substrate (0.5 mmol), and THF (1 mL) were added to a 1.7 mL sample vial and shaken to ensure full dissolution. The vial was placed under blue light radiation for 48 h and then allowed to cool to room temperature. Yields determined by 1H-NMR spectroscopy ofthe crude reaction mixtures using 1,3,5-trimethoxybenzene as an internal standard [0.5 mL; standard solution = 1,3,5-trimethoxybenzene (0.336 g, 2.0 mmol) in diethyl ether (10 mL)]. Product ratios were determined by 1H-NMR spectroscopy of the crude reaction mixtures.
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