Molecular Formula | C16H13N5O2 |
Molar Mass | 307.31 |
Density | 1.344±0.06 g/cm3(Predicted) |
Melting Point | 188-193°C |
Boling Point | 546.6±60.0 °C(Predicted) |
Appearance | Solid |
Color | Yellow |
pKa | 2.68±0.12(Predicted) |
Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
Physical and Chemical Properties | N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidinamine has a melting point of 188-193°C and a boiling point of 546.6±60.0°C(Predicted), the density was 1.344±0.06g/cm3(Predicted, and the acidity coefficient (pKa) was 2.68±0.12(Predicted). |
Uses | N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidamines are a very important class of heterocyclic compounds, widely used in biology, medicine and agriculture and other fields. Studies have shown that the compound has good biological activities, such as sterilization, insecticidal, weeding, anti-virus, anti-cancer, etc. It is also used as a precursor for the synthesis of some important anti-cancer drugs, such as imatinib, which is a selective casinic acid kinase inhibitor mainly used in the treatment of chronic spinal leukemia and gastrointestinal stromal tumors. |
Synthesis method | Step 1: The preparation of 1-(2-methyl -5-nitrophenyl) guanidinyl -2-methyl -5-nitroaniline-(50g,0.328 mol) and n-butanol (200ml) is placed in a reaction bottle. 35% concentrated hydrochloric acid (19ml) was slowly added to the reaction mass for 15 minutes. Stir the reactants for 15 minutes, and slowly add 50% aqueous cyanamide (82.3ml,1.978 moles) to the reactants for 15 minutes. The reaction mixture was heated to 90-95°C and stirred at the same temperature for four hours, and concentrated hydrochloric acid (19ml) was slowly added drop by drop within 15 minutes. The reaction mixture was stirred further for four hours while maintaining the temperature at 90-95°C. Concentrated hydrochloric acid (29ml) was added drop by drop, and the reaction mixture was kept at 90°C for 4 hours. The reaction mass was maintained at the same temperature for a total of 20 hours. The auxiliary reaction completed the reaction mass was cooled to 10°C and alkalized with 10% aqueous sodium hydroxide solution (400ml). The solid product was filtered, washed with 200ml of water and dried to give 1-(2-methyl-5-nitrophenyl) guanidine. Yield (63g,98.7%). HPLC purity: 99% Step 2: N-(5-nitro-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine -1-(2-methyl-5-nitrophenyl) guanidine (63g, the preparation of 0.324 mol), 3-dimethylamino-1-(3-pyridine)-2-propen-1-one (62.5g,0.357) and n-butanol (560ml) was placed in a reaction bottle. The reaction mixture was heated to 120°C for 9 hours. The reaction mass was adjusted to room temperature, water (450ml) was added, and stirred at room temperature for 3-4 hours. The precipitated solids were separated by filtration and dried to give N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidinamine. Yield (73.7g, 81.9%). HPLC purity: 99.9%. Figure N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidinamine synthesis route. |