2-AMINO-3-(METHYLAMINO)PYRAZINE

A mixture of 25 (5.20 g, 40.1 mmol) and CuSOTo a mixture of 26 (3.99 g, 32.1 mmol) in THF (200 mL) was added carbonyldiimidazole (CDI; 10.4 g, 64.1 mmol), and the mixture was stirred at 70 C for 5 h. The reaction mixture was allowed to cool to room temperature and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 0-5% MeOH in CHCl3). The residue was washed with EtOAc/n-hexane. To the residue in MeCN (100 mL) were added ethyl acrylate (7.00 mL, 64.4 mmol) and DBU (2.40 mL, 16.4 mmol), and the mixture was stirred at 50 C for 12 h under argon atmosphere. The mixture was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 0-5% MeOH in CHCl3) to give 27 (6.11 g, 76%) as a colorless solid. 1H NMR (DMSO-d6) delta 1.10 (t, 3H, J = 7.1 Hz), 2.81 (t, 2H, J = 7.1 Hz), 3.34 (s, 3H), 4.00 (q, 2H, J = 7.1 Hz), 4.11 (t, 2H, J = 7.1 Hz), 7.95 (d, 1H, J = 3.3 Hz), 7.96 (d, 1H, J = 3.3 Hz); MS (ESI) m/z 251 [M+H]+.A mixture of 25 (5.20 g, 40.1 mmol) and CuSO4 (640 mg, 4.01 mmol) in 12 M methanamine aqueous solution (40.0 mL, 480 mmol) was stirred at 120 C for 3 h under microwave irradiation. The reaction mixture was allowed to cool to room temperature and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 0-5% MeOH in CHCl3) to give 26 (3.99 g, 80%) as a yellow solid. 1H NMR (DMSO-d6) delta 2.81 (d, 3H, J = 4.7 Hz), 5.84 (s, 2H), 6.13 (q, 1H, J = 4.7 Hz), 7.09 (d, 1H, J = 3.1 Hz), 7.23 (d, 1H, J = 3.1 Hz); MS (ESI) m/z 125 [M+H]+.

Molecular Weight:124.14
XLogP3:-0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:124.074896272
Monoisotopic Mass:124.074896272
Topological Polar Surface Area:63.8
Heavy Atom Count:9
Complexity:85
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes