1193-21-1 Usage
Description
4,6-Dichloropyrimidine, with the CAS number 1193-21-1, is a yellow solid compound known for its utility in various organic synthesis processes. It exhibits unique chemical properties, as evidenced by its cyclic voltammograms that show three cathodic waves resulting from the sequential cleavage of carbon-chlorine bonds and the reduction of the pyrimidine ring.
Uses
Used in Organic Synthesis:
4,6-Dichloropyrimidine is used as a key compound in organic synthesis, serving as a versatile building block for the creation of more complex molecules. Its chemical properties make it a valuable asset in the synthesis of a wide range of compounds.
Used in Synthesis of N-substituted Azacalix[4]pyrimidines:
In the field of macrocyclic chemistry, 4,6-dichloropyrimidine is utilized as a starting reagent for the synthesis of N-substituted azacalix[4]pyrimidines. These macrocyclic compounds have potential applications in various areas, including supramolecular chemistry and molecular recognition.
Used in Synthesis of Disubstituted Pyrimidines:
4,6-Dichloropyrimidine is also employed in the synthesis of disubstituted pyrimidines through a tandem amination and Suzuki-Miyaura cross-coupling process. Disubstituted pyrimidines are important intermediates in the development of pharmaceuticals and agrochemicals, as they can be further modified to create a variety of biologically active molecules.
Used in Biarylpyrimidine Synthesis:
In the synthesis of biarylpyrimidines, which are compounds with potential applications in medicinal chemistry, 4,6-dichloropyrimidine is used as a starting material. The biaryl cross-coupling process allows for the formation of biarylpyrimidine derivatives, which can be further functionalized and studied for their potential therapeutic properties.
Synthesis
The synthesis of 4,6-Dichloropyrimidine is as follows:Dissolve 105.5g of 4,6-diaminopyrimidine in 660.0g of 31% hydrochloric acid and pour into a 2000ml bottle to cool to -5 ° C and dropwise add 500.3g of 33% sodium nitrite. After 2 hours of reaction, HPLC detects 4,6-diamino Pyrimidine is less than 0.5%. 42.8 g of cuprous chloride and 214.0 g of 31% hydrochloric acid are prepared in a 2000 ml bottle. The diazonium salt mother liquor is added dropwise to the bottle. After the dropwise reaction, the reaction is performed at 45 ° C for 2 hours. .Extract with 400g of recovered trichloroethane (200x2 times less than new ones), combine the organic layers for distillation, control the water flush pump 5KPa, temperature 40-140 , collect 404.2g of solvent in the early 40-90 , 90-140 in the later The product was collected at a temperature of 14 ° C to obtain 146.9 g of 4,6-dichloropyrimidine. The yield was 86.4% (based on formazan hydrochloride) and the purity was 99.4%.
Check Digit Verification of cas no
The CAS Registry Mumber 1193-21-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,9 and 3 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1193-21:
(6*1)+(5*1)+(4*9)+(3*3)+(2*2)+(1*1)=61
61 % 10 = 1
So 1193-21-1 is a valid CAS Registry Number.
InChI:InChI:1S/C4H2Cl2N2/c5-3-1-4(6)8-2-7-3/h1-2H
1193-21-1Relevant articles and documents
The efficient one-step chlorination of methylsulfanyl group on pyrimidine ring system with sulfuryl chloride
Ham, Young Jin,Lee, Duck-Hyung,Choi, Hwan Geun,Hah, Jung-Mi,Sim, Taebo
, p. 4609 - 4611 (2010)
A facile one-step transformation of methylsulfanyl and arylsulfanyl groups on pyrimidine ring system into the corresponding chloride group was achieved using sulfuryl chloride in acetonitrile/dichloromethane.
4,6-dichloropyrimidine preparation method
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Paragraph 0044; 0046; 0047; 0048; 0050; 0051; 0052; 0054, (2020/02/14)
The invention discloses a 4,6-dichloropyrimidine preparation method, which comprises: carrying out a cyclization reaction on a compound represented by a formula I and malononitrile in a sodium alcoholate system, evaporating to remove the alcohol after the cyclization reaction, adding water to dissolve, regulating the pH value with an acid, and carrying out cooling crystallization to obtain a compound represented by a formula II, wherein in the compound represented by a formula I, X is HCl, HNO3, H2SO4 or acetic acid; and adding hydrochloric acid and sodium nitrite into the compound representedby the formula II, carrying out a diazotization reaction, carrying out a Sandmeyer reaction under catalysis, extracting with a polar solvent after the reaction, and distilling to obtain a compound represented by a formula III, ie., 4,6-dichloropyrimidine.
Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis
Wang, Jian,Li, Yan-Hui,Pan, Song-Cheng,Li, Ming-Fang,Du, Wenting,Yin, Hong,Li, Jing-Hua
supporting information, p. 146 - 153 (2020/03/10)
The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.
Design, synthesis, and anticancer evaluation of acetamide and hydrazine analogues of pyrimidine
Chashoo, Gousia,Khazir, Jabeena,Maqbool, Tariq,Mir, Bilal Ahmad,Pilcher, Lynne,Riley, Darren
, (2020/02/05)
A library of acetamide and hydrazine analogues were generated on the pyrimidine ring through a multistep reaction starting from 5-nitro-pyrimidine-4,6-diol and pyrimidine-4,6-diol, respectively. The synthesized analogues were screened for in vitro cytotoxic activity against various human cancer cell lines like HCT-1 and HT-15 (colon), MCF-7(breast), PC-3 (prostrate), SF268 (CNS) using MTT method. From the bioassay results, it was observed that even though many of the synthesized derivatives exhibited a good potency against various screened cancer cell lines, compound 14a from the acetamide series was found to show potent anticancer activity on all the tested cancer cell lines with IC50 value of 0.36μM on CNS cell line and 1.6μM on HT-21 cell line, and compound 19xxi from hydrazine series of pyrimidine showed potent activity against three tested cancer cell lines with IC50 value of 0.76μM on HT-29 cell line, 2.6μM on HCT-15, and 3.2μM on MCF-7 cell line.