3-AMINOPYRAZINE-2-CARBONITRILE

Compound 1d (1 mmol, 120 mg), [HDBN+][TFE-] (6 mmol, 1.35 g)was added to a 10 ml round-bottomed flask.in CO2 Under the environment, the reaction was heated to 90C for 20 hours, and the reaction was stopped. After the temperature was cooled to room temperature, saturated NH was added.4Aqueous Cl solution to adjust the pH to neutral, respectively 20ml CH2Cl2Extract three times and collect CH2Cl2The solution was dried over anhydrous sodium sulfate, filtered, and the solution was evaporated under reduced pressure. The solid was isolated by silica gel column chromatography (eluent CH2Cl2:CH3OH=15:1) 141 mg of pale yellow solid compound 2d was obtained with a yield of 86%.General procedure: Substrate (1.0 mmol), [HDBN+][TFE-] (6.0 mmol) were loaded in a 10 mL glass reaction tube equipped with a magnetic stirrer. The air in the reactor was replaced by CO2. Then, the reactor was stirred at the desired temperature for 3-96 h under CO2 using a balloon. After the reaction, the reaction liquid was cooled to room temperature and quenched by saturated ammonium chloride solution. Then the mixture was filtered to afford the crude product, which was purified by chromatography (silica gel, methanol/dichloromethane=1/20) to give the desired compound. The purified product was characterized by NMR and HR-MS. 1H NMR and 13C NMR studies were carried out with a JEOL NMR 400 (400 MHz, 100 MHz) spectrometer with DMSO-d6 as the solvent. Mass spectra were recorded with an AMD40223(Interambulacra) spectrometer.d) 4-Amino-2-[(2, 3-dichlorophenoxy)methyl]pteridine Obtained using the procedure described in section c of Example 2, starting with 3.6 g (0.030 mole) of 3-amino-2-pyrazinecarbonitrile and 6.6 g (0.030 mole) of 2-(2, 3-dichlorophenoxy)acetamidine in 100 ml of absolute ethanol. Refluxing time: 14 hours. Yld: 8.1 g (84%), m.p. 216-218 C. (ethanol). NMR (DMSO-d6): delta=5.2 (2H, s); 7.1 (3H, s); 8.3 (2H, peak exchangeable with CF3 COOD); 8.7 (1H, d); 9.0 (1H, d).d) 2-[(4-Acetyl-3-hydroxy-2-propylphenoxy)methyl]-4-aminopteridine Obtained using the procedure described in section c of Example 2, starting with 3.6 g (0.030 mole) of 3-amino-2-pyrazinecarbonitrile and the above solution of 2-(4-acetyl-3-hydroxy-2-propylphenoxy)acetamidine in absolute ethanol. Refluxing time: 6 hours. Yld: 3.2 g (30%), m.p. 178-180 C. (ethanol/N, N-dimethylformamide). An analytic sample was obtained by a further recrystallization from a mixture of ethanol and N, N-dimethylformamide. M.p. 179-181 C. IR: nu (C=0)=1640 cm-1. NMR (DMSO-d6): delta=0.9 (3H, t); 1.1-1.9 (2H, m); 2.5 (3H, s); 2.5-2.9 (2H, m); 5.2 (2H, s); 6.6 (1H, d); 7.7 (1H, d); 8.3 (2H, peak exchangeable with CF3 COOD); 8.8 (1H, d); 9.0 (1H, d); 13.9 (1H, peak exchangeable with CF3 COOD).c) 4-Amino-2-[(3, 4-dichlorophenoxy)methyl]pteridine Obtained using the procedure described in section c of Example 2, starting with 9.6 g (0.080 mole) of 3-amino-2-pyrazinecarbonitrile and 26.3 g (0.12 mole) of 2-(3, 4-dichlorophenoxy)acetamidine in 520 ml of absolute ethanol. Refluxing time: 3 hours. Yld: 18.0 g (70%), m.p. 261-263 C. (ethanol/N, N-dimethylformamide). NMR (CF3 COOD): delta=5.4 (2H, s); 6.9-7.6 (3H, m); 9.2 (2H, s).d) 4-Amino-2-[(2, 2, 2-trifluoroethoxy)methyl]pteridine Obtained using the procedure described in section c of Example 2, starting with 7.2 g (0.060 mole) of 3-amino-2-pyrazinecarbonitrile and 14.2 g (0.091 mole) of 2-(2, 2, 2-trifluoroethoxy)acetamidine in 230 ml of absolute ethanol. Refluxing time: 7 hours. Yld: 6.5 g (42%), m.p. 145-147 C. (ethyl acetate). NMR (DMSO-d6): delta=4.2 (2H, q); 4.6 (2H, s); 8.3 (2H, peak exchangeable with CF3 COOD); 8.7 (1H, m); 9.0 (1H, m).

Molecular Weight:120.11
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:120.043596145
Monoisotopic Mass:120.043596145
Topological Polar Surface Area:75.6
Heavy Atom Count:9
Complexity:135
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes