Category: pyrimidines

Liu, Ju; Wu, Shuang; Wang, Huan; Du, Si-Yuan; Li, Zhen; Shen, Ji-Wei; Chen, Ye; Ding, Shi published an article in 2022. The article was titled 《Novel 2,4-diarylaminopyrimidine derivatives containing pyridine moiety: design, synthesis, crystal structure and biological evaluation》, and you may find the article in Chinese Journal of Structural Chemistry.Electric Literature of C4H2Cl2N2 The information in the text is summarized as follows:

A series of 2,4-diarylaminopyrimidine derivatives I [R = H, 4-Me, 4-F, etc.] containing pyridine structure were designed and synthesized. The crystal structures of compounds I [R = 3-Cl, 4-F-3-Cl] were obtained from X-ray diffraction. The crystal structure of I [R = 3-Cl] (C25H20ClFN6O2) belongs to the monoclinic system, space group P21/c with a = 11.0500(10), b = 18.3045(17), c = 13.5646(9) Å and β = 122.806(5)°. I [R = 4-F-3-Cl] (C25H19ClF2N6O2) was of monoclinic system, space group P21/c with a = 10.9998(18), b = 18.517(3), c = 13.6355(16) Å and β = 123.315(9)°. The bioassay results showed all of the target compounds I exhibited potential antiproliferative activities against MKN-45, HT-29, A549, K562 and GIST882 cell lines. Among them, compounds I [R = H, 4-Cl, 4-F-3-Cl] exhibited remarkable inhibitory activities against GIST882, K562 and A549 cell lines with IC50 values of 0.68, 0.38 and 0.60μM, resp., which were comparable to that of the pos. control foretinib. The results came from multiple reactions, including the reaction of 2,4-Dichloropyrimidine(cas: 3934-20-1Electric Literature of C4H2Cl2N2)

2,4-Dichloropyrimidine(cas: 3934-20-1) is a member of organic chlorides. Almost all organochlorine compounds are synthesized. It is widely used as intermediates, solvents and pesticides of chemical synthetic products.Electric Literature of C4H2Cl2N2

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In 2018,El-Kalyoubi, Samar A. published 《Synthesis and anticancer evaluation of some novel pyrimido[5,4-e][1,2,4]triazines and pyrazolo[3,4-d]pyrimidine using DMF-DMA as methylating and cyclizing agent》.Chemistry Central Journal published the findings.Related Products of 3764-01-0 The information in the text is summarized as follows:

A series of pyrimido[5,4-e][1,2,4]triazines I (R1 = Ph, 4-ClC6H4, 4-BrC6H4, 4-HOC6H4, 4-O2NC6H4) was obtained via condensation of 6-hydrazinyluracil with various benzaldehydes to give the hydrazones II (R2 = H) followed by nitrosation with HNO2 and intramol. cyclization. On the other hand, pyrazolopyrimidine III (R3 = 1-phenylvinyl) was obtained by the reaction of hydrazone II (R1 = Ph; R2 = Me) with DMF-DMA via formation of the intermediate IV whereas the compound III (R3 = Me) was prepared by refluxing hydrazinyluracil with DMF-DMA in DMF directly. The newly synthesized compounds I, II, III and IV were evaluated in-vitro for their anticancer activity against human lung carcinoma (A549). The compound I (R1 = 4-ClC6H4) showed the highest effect with IC50 value 3.6 μM, followed by compounds III (R3 = 1-phenylvinyl), II (R1 = R2 = H), IV, II (R1 = 4-O2NC6H4; R2 = H) and I (R1 = 4-O2NC6H4). After reading the article, we found that the author used 2,4,6-Trichloropyrimidine(cas: 3764-01-0Related Products of 3764-01-0)

2,4,6-Trichloropyrimidine(cas: 3764-01-0) is a member of organic chlorides. Almost all organochlorine compounds are synthesized. It is widely used as intermediates, solvents and pesticides of chemical synthetic products.Related Products of 3764-01-0

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In 2016,Cheng, Hengmiao; Nair, Sajiv K.; Murray, Brion W.; Almaden, Chau; Bailey, Simon; Baxi, Sangita; Behenna, Doug; Cho-Schultz, Sujin; Dalvie, Deepak; Dinh, Dac M.; Edwards, Martin P.; Feng, Jun Li; Ferre, Rose Ann; Gajiwala, Ketan S.; Hemkens, Michelle D.; Jackson-Fisher, Amy; Jalaie, Mehran; Johnson, Ted O.; Kania, Robert S.; Kephart, Susan; Lafontaine, Jennifer; Lunney, Beth; Liu, Kevin K.-C.; Liu, Zhengyu; Matthews, Jean; Nagata, Asako; Niessen, Sherry; Ornelas, Martha A.; Orr, Suvi T. M.; Pairish, Mason; Planken, Simon; Ren, Shijian; Richter, Daniel; Ryan, Kevin; Sach, Neal; Shen, Hong; Smeal, Tod; Solowiej, Jim; Sutton, Scott; Tran, Khanh; Tseng, Elaine; Vernier, William; Walls, Marlena; Wang, Shuiwang; Weinrich, Scott L.; Xin, Shuibo; Xu, Haiwei; Yin, Min-Jean; Zientek, Michael; Zhou, Ru; Kath, John C. published 《Discovery of 1-{(3R,4R)-3-[({5-Chloro-2-[(1-methyl-1H-pyrazol-4-yl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)methyl]-4-methoxypyrrolidin-1-yl}prop-2-en-1-one (PF-06459988), a Potent, WT Sparing, Irreversible Inhibitor of T790M-Containing EGFR Mutants》.Journal of Medicinal Chemistry published the findings.HPLC of Formula: 90213-66-4 The information in the text is summarized as follows:

First generation EGFR TKIs (gefitinib, erlotinib) provide significant clin. benefit for NSCLC cancer patients with oncogenic EGFR mutations. Ultimately, these patients’ disease progresses, often driven by a second-site mutation in the EGFR kinase domain (T790M). Another liability of the first generation drugs is severe adverse events driven by inhibition of WT EGFR. As such, our goal was to develop a highly potent irreversible inhibitor with the largest selectivity ratio between the drug-resistant double mutants (L858R/T790M, Del/T790M) and WT EGFR. A unique approach to develop covalent inhibitors, optimization of reversible binding affinity, served as a cornerstone of this effort. PF-06459988 was discovered as a novel, third generation irreversible inhibitor, which demonstrates (i) high potency and specificity to the T790M-containing double mutant EGFRs, (ii) minimal intrinsic chem. reactivity of the electrophilic warhead, (iii) greatly reduced proteome reactivity relative to earlier irreversible EGFR inhibitors, and (iv) minimal activity against WT EGFR. After reading the article, we found that the author used 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine(cas: 90213-66-4HPLC of Formula: 90213-66-4)

2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine(cas: 90213-66-4) belongs to pyrimidine. Pyrimidine derivatives also play an important role in drug development, either in concert with other compounds or on their own. HPLC of Formula: 90213-66-4They have been used in a wide variety of pharmaceuticals including general anesthetics, anti-epilepsy medication, anti-malaria medication, drugs for treating high blood pressure, and HIV medication.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The author of 《Useful preparations involving the reactions of nucleophiles with trimethylammonio derivatives of nitrogen heterocycles》 were Barlin, G. B.; Young, A. C.. And the article was published in Journal of the Chemical Society in 1972. Quality Control of 2-Methoxy-5-nitropyrimidine The author mentioned the following in the article:

Alkoxy, amino, propylamino, hydrazino, mercapto, fluoro, and cyano derivatives of pyridine, pyrimidine, quinoline, quinazoline, and purine were prepared by treatment of the corresponding trimethylammonio compound with the appropriate nucleophile; thus, 71% 4-(propyl-amino)pyrimidine was prepared from trimethyl-4-pyrimidinyl-ammonium salt and PrNH2. In the part of experimental materials, we found many familiar compounds, such as 2-Methoxy-5-nitropyrimidine(cas: 14001-69-5Quality Control of 2-Methoxy-5-nitropyrimidine)

2-Methoxy-5-nitropyrimidine(cas: 14001-69-5) is a member of ether. When aromatic ethers are exposed to halogen in the presence or absence of a catalyst, they undergo halogenation, such as bromination.Quality Control of 2-Methoxy-5-nitropyrimidine

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Wang, Yujie; Rong, Jie; Zhang, Bin; Hu, Liming; Wang, Xiaoli; Zeng, Chengchu published an article on February 15 ,2015. The article was titled 《Design and synthesis of N-methylpyrimidone derivatives as HIV-1 integrase inhibitors》, and you may find the article in Bioorganic & Medicinal Chemistry.Application In Synthesis of Methyl 2-benzyl-5,6-dihydroxypyrimidine-4-carboxylate The information in the text is summarized as follows:

A series of novel β-diketo derivatives which combined the virtues of dihydroxypyrimidine carboxamide derived from the evolution of diketo acids and polyhydroxylated aromatics moieties were designed and synthesized as potential HIV-1 integrase (IN) inhibitors and their inhibition to the strand transfer process of HIV-1 integrase and anti-HIV-1 activity evaluated. The result indicates that 3,4,5-trihydroxylated aromatic derivatives exhibit good inhibition to HIV-1 integrase, but dihydroxylated aromatic derivatives show little inhibition to HIV-1 integrase. In addition, the preliminary structure-activity relationship (SAR) of these new derivatives was rationalized by docking studies.Methyl 2-benzyl-5,6-dihydroxypyrimidine-4-carboxylate(cas: 519032-07-6Application In Synthesis of Methyl 2-benzyl-5,6-dihydroxypyrimidine-4-carboxylate) was used in this study.

Methyl 2-benzyl-5,6-dihydroxypyrimidine-4-carboxylate(cas: 519032-07-6) belongs to pyrimidine. The pyrimidine ring system has wide occurrence in nature as substituted and ring fused compounds and derivatives, including the nucleotides cytosine, thymine and uracil, thiamine (vitamin B1) and alloxan. Application In Synthesis of Methyl 2-benzyl-5,6-dihydroxypyrimidine-4-carboxylate

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Quality Control of 3-(Pyrimidin-5-yl)benzaldehydeOn March 10, 2016, Wu, Yong-Jin; Guernon, Jason; Yang, Fukang; Snyder, Lawrence; Shi, Jianliang; McClure, Andrea; Rajamani, Ramkumar; Park, Hyunsoo; Ng, Alicia; Lewis, Hal; Chang, Chieh Ying; Camac, Dan; Toyn, Jeremy H.; Ahlijanian, Michael K.; Albright, Charles F.; Macor, John E.; Thompson, Lorin A. published an article in ACS Medicinal Chemistry Letters. The article was 《Targeting the BACE1 Active Site Flap Leads to a Potent Inhibitor That Elicits Robust Brain Aβ Reduction in Rodents》. The article mentions the following:

By targeting the flap backbone of the BACE1 active site, the authors discovered 6-dimethylisoxazole-substituted biaryl aminothiazine I with 34-fold improved BACE1 inhibitory activity over the lead compound The cocrystal structure of I bound to the active site indicated two hydrogen-bond interactions between the dimethylisoxazole and threonine 72 and glutamine 73 of the flap. Incorporation of the dimethylisoxazole substitution onto the related aminothiazine carboxamide series led to pyrazine-carboxamide II as a very potent BACE1 inhibitor (IC50 < 1 nM). This compound demonstrated robust brain Aβ reduction in rat dose-response studies. Thus, compound II may be useful in testing the amyloid hypothesis of Alzheimer's disease. The experimental process involved the reaction of 3-(Pyrimidin-5-yl)benzaldehyde(cas: 640769-70-6Quality Control of 3-(Pyrimidin-5-yl)benzaldehyde)

3-(Pyrimidin-5-yl)benzaldehyde(cas: 640769-70-6) belongs to pyrimidine. Pyrimidine nucleotide derivatives have a wide range of biological applications. For example, pyrimidine derivatives are useful in DNA repair studies involving cancer and epigenetics. Quality Control of 3-(Pyrimidin-5-yl)benzaldehyde

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In 2018,Journal of Physical Organic Chemistry included an article by Yuan, Hua; Li, Meng-Yang; Chen, Chun-Ni; Zhang, Yan; Liu, Wan-Qiang. Recommanded Product: 14001-69-5. The article was titled 《Substituent effects on the UV absorption energy of 2,5-disubstituted pyrimidines》. The information in the text is summarized as follows:

Pyrimidine-containing mols. have been extensively investigated in organic light emitting devices (OLEDs), solar cells, liquid crystals, and so on due to their perfect photoelec. properties. UV absorption is one of the interesting photoelec. properties. Systematical study of the substituent effects on the UV absorption energy of pyrimidine derivatives will guide to design functional mols. with specific photoelec. properties. In this paper, thirty-seven 2-X-5-Y pyrimidines with various substituents (X/Y=NH2, CH3, OCH3, NMe2, CF3, NO2, Cl, Br, I) were synthesized, and their UV spectra were recorded in anhydrous ethanol. The maximum absorption wavelength λmax(nm) were obtained and converted to wavenumber νmax(cm-1) (νmax = 1/λmax) for quant. structure-property relationship study. Hammett parameters (σ, σF, σR), electronegativity (χ), the excited-state substituent effect parameter (σCCex), and the heavy atom effect indicator (D) were employed as descriptors characterizing the mol. structure. By stepwise regression, a 5-descriptor linear regression model was built as νmax = 35 864.8122 + 6743.7901σR(X) + 8587.9937σR(Y) – 2042.7280Δσ2 + 1106.0034D(X) + 1451.8873χ(X) (R = 0.9861, S = 693.70, ARD = 1.49%, F = 218.68, Rcv = 0.9775, Scv = 881.25, ARDcv = 1.82%, n = 37). The model is proved of good stability and predictive performance by leave-one-out cross validation. Compared with the benzylideneaniline derivatives with CN bridge group, the substituent effects on the UV absorption energy of 2,5-disubstituted pyrimidines are quite different and much more complex. In the experiment, the researchers used 2-Methoxy-5-nitropyrimidine(cas: 14001-69-5Recommanded Product: 14001-69-5)

2-Methoxy-5-nitropyrimidine(cas: 14001-69-5) is a member of ether. Friedel Crafts reaction, for example, adds an alkyl or acyl group to aromatic ethers when they react with an alkyl or acyl halide in the presence of a Lewis acid as a catalyst.Recommanded Product: 14001-69-5

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In 1977,Chemical & Pharmaceutical Bulletin included an article by Kato, Tetsuo; Oda, Noriichi; Ito, Isoo. Reference of 2-Methoxy-6-methylpyrimidin-4-amine. The article was titled 《Synthesis of compounds related to antitumor agents. VI. The conversion of 2,4-dialkoxypyrimidines into N-dialkyl-1,2,3,4-tetrahydro-2,4-dioxopyrimidines in the presence of p-toluenesulfonic acid derivatives》. The information in the text is summarized as follows:

Twelve 2,4-dialkoxypyrimidines I (R1 = Me, Et, Pr, allyl; R2 = Me, H; R3 = H, Br) were converted into 1,3-dialkyl-1,2,3,4-tetrahydro-2,4-dioxopyrimidines II by heating in the presence of p-MeC6H4SO3H or its derivatives, whereas III under similar conditions gave IV and V. In addition to this study using 2-Methoxy-6-methylpyrimidin-4-amine, there are many other studies that have used 2-Methoxy-6-methylpyrimidin-4-amine(cas: 51870-75-8Reference of 2-Methoxy-6-methylpyrimidin-4-amine) was used in this study.

2-Methoxy-6-methylpyrimidin-4-amine(cas: 51870-75-8) belongs to anime. Acylation is one of the most important reactions of primary and secondary amines; a hydrogen atom is replaced by an acyl group (a group derived from an acid, such as RCOOH or RSO3H, by removal of ―OH, such as RC(=O)―, RS(O)2―, and so on). Reagents may be acid chlorides (RCOC1, RSO2C1), anhydrides ((RCO)2O), or even esters (RCOOR′); the products are amides of the corresponding acids.Reference of 2-Methoxy-6-methylpyrimidin-4-amine

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In 1966,Journal of Organic Chemistry included an article by Temple, Carroll Jr.; Montgomery, John A.. Formula: C6H7Cl2N3. The article was titled 《Some unusual reactions of 6-chloropurines with thioureas. 6-Alkylthiopurines and 2,2-diamino-2H-thiazolo[3,4,5-gh]purines from 2-(purin-6-yl)-2-thiopseudoureas》. The information in the text is summarized as follows:

Reaction of 6-chloropurine (I) with thiourea gave, in addition to purine-6(1H)-thione (II), 2,2-diamino-2H-thiazolo[3,4,5-gh]purine (III). 1-Ethyl-2-thiourea and I provided the corresponding ethyl derivative of III. From the reaction of 6-chloro-2-ethylpurine and thiourea in PrOH, 2-ethylpurine-6(1 H)-thione, 2,2-diamino-7-ethyl-2H-thiazolo[3,4,5-gh]purine, and 2-ethyl-6-(propylthio)purine (IV) were obtained, the formation of IV resulting from solvent participation. 6-Chloro-2,9-diethylpurine and thiourea in PrOH gave 2,9-diethyl-2-(propylthio)purine as a major component. Treatment of I, 2,6-dichloropurine, and 2-amino-6-chloropurine with 2-imidazolidinethione gave the corresponding 6-(2-imidazolinylthio)purine hydrochlorides (V, VI, and VII), resp. The free base of V and VI but not of VII appeared to form derivatives of III by intramol. addition Basic hydrolysis converted V to II, VI to 2-chlorohypoxanthine, and VII to thioguanine containing a trace of guanine. The results came from multiple reactions, including the reaction of 4,6-Dichloro-2-ethylpyrimidin-5-amine(cas: 6237-96-3Formula: C6H7Cl2N3)

4,6-Dichloro-2-ethylpyrimidin-5-amine(cas: 6237-96-3) belongs to anime. Nitrous acid converts secondary amines (aliphatic or aromatic) to N-nitroso compounds (nitrosamines): R2NH + HNO2 → R2N―NO. Some nitrosamines are potent cancer-inducing substances, and their possible formation is a serious consideration when nitrites, which are salts of nitrous acid, are present in foods or pharmaceutical preparations. Tertiary amines give rise to nitrosamines more slowly; an alkyl group is eliminated as an aldehyde or ketone, along with nitrous oxide, N2O.Formula: C6H7Cl2N3

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

SDS of cas: 519032-07-6On November 16, 2006 ,《4,5-Dihydroxypyrimidine Carboxamides and N-Alkyl-5-hydroxypyrimidinone Carboxamides Are Potent, Selective HIV Integrase Inhibitors with Good Pharmacokinetic Profiles in Preclinical Species》 appeared in Journal of Medicinal Chemistry. The author of the article were Summa, Vincenzo; Petrocchi, Alessia; Matassa, Victor G.; Gardelli, Cristina; Muraglia, Ester; Rowley, Michael; Paz, Odalys Gonzalez; Laufer, Ralph; Monteagudo, Edith; Pace, Paola. The article conveys some information:

The dihydroxypyrimidine carboxamide 4a was discovered as a potent and selective HIV integrase strand transfer inhibitor. The optimization of physicochem. properties, pharmacokinetic profiles, and potency led to the identification of (I) in the dihydroxypyrimidine series and (II) in the N-methylpyrimidinone series having low nanomolar activity in the cellular HIV spread assay in the presence of 50% normal human serum and very good pharmacokinetics in preclin. species. After reading the article, we found that the author used Methyl 2-benzyl-5,6-dihydroxypyrimidine-4-carboxylate(cas: 519032-07-6SDS of cas: 519032-07-6)

Methyl 2-benzyl-5,6-dihydroxypyrimidine-4-carboxylate(cas: 519032-07-6) belongs to pyrimidine. Pyrimidine derivatives also play an important role in drug development, either in concert with other compounds or on their own. SDS of cas: 519032-07-6They have been used in a wide variety of pharmaceuticals including general anesthetics, anti-epilepsy medication, anti-malaria medication, drugs for treating high blood pressure, and HIV medication.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia