Molecular Formula | C5H3ClN4 |
Molar Mass | 154.56 |
Density | 1.53±0.1 g/cm3(Predicted) |
Melting Point | 200 °C (dec.) (lit.) |
Boling Point | 435.0±30.0 °C(Predicted) |
Solubility | DMF, DMSO, Methanol, Water |
Appearance | Powder or Flakes |
Color | Brown |
pKa | -0.68±0.10(Predicted) |
Storage Condition | 2-8°C(protect from light) |
MDL | MFCD00052343 |
Hazard Symbols | Xn - Harmful |
Risk Codes | R22 - Harmful if swallowed R37/38 - Irritating to respiratory system and skin. R41 - Risk of serious damage to eyes R43 - May cause sensitization by skin contact |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
UN IDs | UN3439 |
WGK Germany | 3 |
HS Code | 29335990 |
Hazard Note | Harmful |
Hazard Class | 6.1 |
Packing Group | III |
background | pyrimidine is a very important heterocyclic compound, widely used in the fields of medicine and pesticides. A large number of studies have shown that these compounds have good biological activities, such as insecticidal, sterilization, weeding, anti-virus, anti-cancer, etc. In recent years, due to the advantages of high efficiency, low toxicity and unique mode of action, the molecular design, synthesis and biological activity research of pyrimidine compounds are still a very active field in the research of heterocyclic compounds. |
preparation | 2,4-dihydroxypyridine -5-ethyl formate (1) was prepared by adding EMME 100g, urea 34.13g, concentrated hydrochloric acid 28.5 mL and ethanol 80 mL into a 1L three-mouth bottle, and stirring at room temperature for 72h. Add 200mL of mixed solution of water and ethanol (plus volume ratio, or directly say what percentage of ethanol) to the reaction solution, stir for 10 min, and filter under reduced pressure to obtain 140.47g of white solid. Transfer the obtained solid into a 1L three-mouth bottle, add 500 mL of water and 40.36 gKOH, stir for 3h at room temperature, adjust pH = 3 with concentrated hydrochloric acid, after stirring for 1h, the temperature is raised to 90 ℃, the white solid is completely dissolved, then cooled to room temperature, filtered under reduced pressure, and dried to obtain 60.3g of white solid with 71.44% yield. Preparation of Ethyl 2, 4-dichloro-5-midpyridine formate (2) 60.3g of compound (1), 35.88g of ammonium tetramethyl silkworm and 180 mL of phosphorus oxychloride were added to a 1L eggplant bottle, and the temperature was raised to 110 ℃ for 5h. Cooling, concentration under reduced pressure, the residue is poured into ice water, pH = 6~7 is adjusted with saturated sodium bicarbonate aqueous solution, extraction with ethyl acetate (500 mL × 2), organic phases are combined, anhydrous magnesium sulfate is dried, and 44.68g of colorless oil is obtained by column chromatography after evaporation to remove solvent, and the yield is 62%. Preparation of 4-Amino -2-Chlorocaridine -5-ethyl formate (3) Add 44.68g of compound (2) and 80mL of tetrahydroenan into a 500 mL three-mouth bottle, cool to -60 ℃, slowly add 20 mL of ammonia water dropwise, react for 3 h, pour the reaction solution into ice water, precipitate white solid, filter under reduced pressure to obtain 35.48g of product, and the yield is 86.9%. Preparation of 4-Amino -2-Chloropyrimidine -5-Nitrile (4) 35.48g of compound (3), 80 mL of tetrahydrofuran and 30 mL of water were added to 500 mL of eggplant bottle, 10.9g of LiOH was slowly added under stirring, and stirred at room temperature for 2 hours after adding. Pour into ice water, extract impurities with ethyl acetate (100 mL× 2), adjust pH = 2 with dilute hydrochloric acid in the water layer, precipitate white solid, filter under reduced pressure to obtain 27.2g of product with 89.1% yield. MS:174.7(M +1), H NMR(DMSO-d4,400 MHz) 8:7.987(s,1 H);8.642(s,1 H). |