Name | 2,6-dichloro-4,8-dipiperidinopyrimido[5,4-d]pyrimidine |
Synonyms | Einecs 230-437-4 2,6-dichloro-4,8-dipiperidinopyrimido[5,4-d]pyrimidine 2,6-Dichloro-4,8-dipiperidinopyrimidino[5,4-d]pyrimidine 2,6-dichloro-4,8-dipiperidinyl-pyrimido[5,4-d]pyrimidine 2,6-dichloro-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine PyriMido[5,4-d]pyriMidine,2,6-dichloro-4,8-di-1-piperidinyl- 2,6-dichloro-4,8-bis(1-piperidinyl)pyrimido[5,4-d]pyrimidine 2,6-Dichloro-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine 2,6-DICHLORO-4,8-DI-1-PIPERIDINYLPYRIMIDO[5,4-D]PYRIMIDINEDIPYRIDAMOLE |
CAS | 7139-02-8 |
EINECS | 230-437-4 |
InChI | InChI=1/C16H20Cl2N6/c17-15-20-12-11(13(21-15)23-7-3-1-4-8-23)19-16(18)22-14(12)24-9-5-2-6-10-24/h1-10H2 |
Molecular Formula | C16H20Cl2N6 |
Molar Mass | 367.28 |
Density | 1.386±0.06 g/cm3(Predicted) |
Melting Point | 249-251℃ |
Boling Point | 504.1±50.0 °C(Predicted) |
Flash Point | 258.7°C |
Vapor Presure | 2.73E-10mmHg at 25°C |
pKa | 2.00±0.30(Predicted) |
Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
Refractive Index | 1.643 |
Physical and Chemical Properties | Crystallization. Melting point 242-250 °c. |
LogP | 2 |
Overview | dipyrimidine, also known as dipyridamole, dipyridamole, dipyridamole, a non-nitrate coronary vasodilator, with the expansion of coronary vessels, promote the formation of collateral circulation and mild anticoagulant effect, with antiviral effect. 2, 6-dichloro-4, 8-dipiperidinopyrido [5,4-D] pyrimidine (dipyridamole) is a key intermediate in the manufacture of Dipyridamole. At present, the synthesis process of 2, 6-dichloro-4, 8-dipiperidinyl pyrimidino [5,4-D] pyrimidine is extensive, with many side reactions and poor quality of synthetic products, the scope of subsequent use of the product is limited. The prior art discloses a method for refining dipyridamole Intermediate 2, 6-dichloro-4, 8-dipiperidinyl pyrimidino [5,4-D] pyrimidine, piperidine has poor selectivity for 2,4,6, 8-tetrachloropyrimidino [5,4-D] pyrimidine, and it is easy to produce a large number of by-products, so it cannot be solved from the root, the synthesis process of 6-dichloro-4, 8-dipiperidinyl pyrimidino [5,4-D] pyrimidine is extensive, with many side reactions and poor quality of the synthesized product. |
preparation | Step 1: 19.6 g2,4,6, 8-tetrahydroxypyrimidino [5,4-d] pyrimidine, ethanol 0.5 ml into the three-port flask with stirrer, temperature, put the three-port flask into the ice water bath, add 38 g4-Toluenesulfonyl chloride, stir the reaction for ~ 1H, after completion of the reaction, ethanol was distilled off under reduced pressure. Add 59.5G piperidine, under the condition of 0 deg C, stirring reaction for 3H, stop the reaction, reduced pressure distillation of excess piperidine, can be reused to obtain compound 3; The 2,4,6, the molar ratio of 8-tetrahydroxypyrimidino [5,4-d] pyrimidine, 4-toluenesulfonyl chloride and piperidine is 1:2:7; Step Two: compound 3 and dichlorosulfoxide, after triethylamine is mixed, it is put into a microwave reactor for reaction, the power of the microwave reactor is 400w, the microwave reaction time is 5min, and the reaction is poured into 0 ℃ cold water while hot, the residue was collected by Suction filtration after naturally warming to room temperature. The molar ratio of compound 3 to dichlorosulfoxide and triethylamine was 1:2:3: the filter residue is washed with a mass fraction of 85% sodium chloride aqueous solution, Suction filtration, and then the filter residue is recrystallized with a mass fraction of 75% ethanol to obtain 2, 6-dichloro-4, 8-dipiperidinopyrido [5,4-D] pyrimidine, yield 89.1%, purity 98.8%. |
Use | an intermediate of piperidine (dipyridamole). |
production method | cyclization of amino-orotic acid with urea to produce 2,4,6, 8-tetrahydroxypyrimidino [5,4-d] pyrimidine is then chlorinated with phosphorus trichloride-phosphorus oxychloride, converted to the corresponding tetrachloride, which is condensed with piperidine to give the product. |