Application of 1458-01-1, A common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, molecular formula is C6H7ClN4O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate 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. Methyl 3,5-diamino-6-phenylpyrazine-2-carboxylate (3a) General Method A using 2 (500 mg, 2.47 mmol) and phenylboronic acid (360 mg, 3.70 mmol) to give 3a (412 mg, 68%) as an off-yellow solid. MP 194-196 C; 1H NMR (500 MHz, DMSO-d6) delta 7.54 (s, 2H), 7.44 (s, 2H), 7.37 (s, 1H), 7.08 (s, 2H), 6.66 (s, 2H), 3.74 (s, 3H); 13C NMR (126 MHz, DMSO-d6) delta 167.3, 156.0, 154.5, 137.6, 130.1, 128.9, 128.5, 128.1, 111.7, 51.4; IR (neat) nu 3435.3, 3319.6, 3160.5, 2948-2852, 1684.9, 1650.1, 1595.2, 1246.1, 708.2, 646.1 cm-1; HRESI-MS m/z (M + H+) Anal for C12H13N4O2+ 245.1033, found 245.1051.
The synthetic route of 1458-01-1 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Buckley, Benjamin J.; Majed, Hiwa; Aboelela, Ashraf; Minaei, Elahe; Jiang, Longguang; Fildes, Karen; Cheung, Chen-Yi; Johnson, Darren; Bachovchin, Daniel; Cook, Gregory M.; Huang, Mingdong; Ranson, Marie; Kelso, Michael J.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 24; (2019);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem