2802-61-1 Usage
Description
2,4-Difluoropyrimidine is an organic compound characterized by the presence of two fluorine atoms at the 2nd and 4th positions of the pyrimidine ring. It serves as a key intermediate in the synthesis of various pharmaceutical compounds and has potential applications in the development of novel drugs.
Uses
Used in Pharmaceutical Industry:
2,4-Difluoropyrimidine is used as a starting material for the synthesis of 3-Pyrimidin-4-yl-oxazolidin-2-one derivatives, which are mutant isocitrate dehydrogenase (IDH1) inhibitors. These inhibitors play a crucial role in the treatment of certain types of cancer by targeting the mutated IDH1 enzyme, which is often found in various malignancies.
Additionally, 2,4-Difluoropyrimidine is used as a starting material for the synthesis of N,N′-(1,4-phenylenebis(methylene))bis(2-fluoropyrimidin-4-amine), which are chemokine receptor type 4 (CXCR4) antagonists. These antagonists have potential applications in the treatment of various diseases, including cancer, by blocking the CXCR4 receptor and disrupting the chemotactic signaling pathways involved in tumor growth and metastasis.
Synthesis
Crown ethers are able to enhance the performance of KF in two ways. Firstly,
they complex the potassium cation making a better fluoride source and secondly they
increase the solubility of KF in the solvent.
KF with a catalytic amount of dicyclohexano-18-crown-6 in tetraglyme converted
2,4-dichloropyrimidine into 2,4-difluoropyrimidine.
Synthesis Reference(s)
Journal of Heterocyclic Chemistry, 22, p. 149, 1985 DOI: 10.1002/jhet.5570220137
Check Digit Verification of cas no
The CAS Registry Mumber 2802-61-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,8,0 and 2 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 2802-61:
(6*2)+(5*8)+(4*0)+(3*2)+(2*6)+(1*1)=71
71 % 10 = 1
So 2802-61-1 is a valid CAS Registry Number.
InChI:InChI=1/C3ClF5/c4-2(6)1(5)3(7,8)9/b2-1+
2802-61-1Relevant articles and documents
The proton sponge-triethylamine tris(hydrogen fluoride) system as a selective nucleophilic fluorinating reagent for chlorodiazines
Darabantu, Mirce,Lequeux, Thierry,Pommelet, Jean-Claude,Plé, Nelly,Turck, Alain,Toupet, Lo?c
, p. 6763 - 6767 (2000)
The proton sponge-triethylamine tris(hydrogen fluoride) mixture provides a mild and efficient fluorinating - reagent for the selective introduction of a fluorine atom, by halogen exchange, into dichlorodiazines. (C) 2000 Elsevier Science Ltd.
Metalation of diazines. XI. Directed ortho-lithiation of fluoropyrimidines and application to synthesis of an azacarboline
Ple,Turck,Heynderickx,Queguiner
, p. 1311 - 1315 (2007/10/02)
For the first time fluoropyrimidines were successfully lithiated. The resulting lithio derivatives were reacted with various electrophiles for the synthesis of new pyrimidines. The synthesis of an azacarboline derivative is reported.