M.W=150-200 | Page 9 of 68

King, F. E.’s team published research in Journal of the Chemical Society in | CAS: 5738-14-7

Journal of the Chemical Society published new progress about 5738-14-7. 5738-14-7 belongs to pyrimidines, auxiliary class Pyrimidine,Amine,Alcohol,Pyrimidine, name is 2-(Dimethylamino)pyrimidine-4,6-diol, and the molecular formula is C6H9N3O2, Application of 2-(Dimethylamino)pyrimidine-4,6-diol.

King, F. E. published the artcileNew potential chemotherapeutic agents. VI. Derivatives of 2,4-diazaacridine, Application of 2-(Dimethylamino)pyrimidine-4,6-diol, the publication is Journal of the Chemical Society (1947), 726-34, database is CAplus and MEDLINE.

cf. C.A. 41, 3107d. Because of the interest in chemotherapy in compounds having a structural resemblance to riboflavin, attention has been turned to 2′,3′,4,5-quinolinopyrimidine, which has been designated 2,4-diazaacridine (cf. Conrad and Reinbach, Ber. 34, 1341(1901)), and especially to derivatives containing basic side chains. Mercaptobarbituric acid (I) (5 g.), 4.5 g. Et₂N(CH₂)₃NH₂, and about 2 mols. freshly prepared Pb(OH)₂ in iso-AmOH, refluxed 15 hrs., give 78% 2-(3-diethylaminopropylamino)-4,6-dihydroxypyrimidine (II), analyzed as the picrolonate, with 1 mol. H₂O (0.5 mol. lost at 100°, 1 mol. at 150°), yellow, m. 235° (decomposition). I (14.4 g.) and 8.4 g. NaHCO₃ in 200 cc. H₂O, shaken 30 min. with 12.6 g. Me₂SO₄ at room temperature, give 72% 4,6-dihydroxy-2-methylmercaptopyrimidine (III); 10 g. crude III and 3.9 g. Et₂N(CH₂)₃NH₂, heated 30 min. at 180°, give 92% II. EtO₂CCH₂CH₂COCl (6 g.) and 5.2 g. Et₂N(CH₂)₃NH₂ in ether at 0° give 60% α-carbethoxy N-(3-diethylaminopropyl)acetamide, b_0.05 115°, did not react with CO(NH₂)₂ in the presence of EtONa in EtOH (6 hrs.). EtO₂CCH₂C(OEt):NH.HCl (6 g.) and 4.2 g. Et₂N(CH₂)₃NH₂ in 100 cc. EtOH 12 hrs. at room temperature give Et₂N(CH₂)₃NHC(:NH)CH₂CO₂Et, whose picrolonate, with 1 mol. H₂O, yellow, m. 125-30°; this could not be condensed with H₂NCO₂Et. The action of Et₂N(CH₂)₃NH₂ on EtO₂CCH₂CONHCONH₂ gives barbituric acid and not Et₂N(CH₂)₂NHCOCH₂CONHCONH₂, which might have been cyclized to a pyrimidine. 2,4,6-Trichloropyrimidine (IV) (3 g.), added to 11 g. PhCH₂OH and 1.15 g. Na in 100 cc. PhMe (after formation of the alcoholate) and the mixture refluxed 2 hrs., gives 63% of the 2,4,6-tris(benzyloxy) derivative, m. 62-4°; the action of Na in liquid NH₃ does not give a pure compound; hydrogenation in AcOH over Pd-charcoal gives 84% barbituric acid. IV (18 g.) in 100 cc. Me₂CO, cautiously treated with 13 g. Et₂N(CH₂)₃NH₂ with cooling, gives 72% 2,6-dichloro-4-(3-diethylaminopropylamino)pyrimidine (V); HCl salt m. 149°; picrate, bright yellow, m. 162°; picrolonate, yellow, m. 164°. V (3.1 g.) and 10 cc. concentrated HCl, heated on the steam bath 12 hrs., give 76% of the di-HCl salt, m. 253° (decomposition), of 6-chloro-4-(3-diethylaminopropylamino)-2-hydroxypyrimidine; picrate, yellow, m. 209° (decomposition). V (6.25 g.), added in 10 portions to PhCH₂ONa (from 13 g. PhCH₂OH and 1.4 g. Na) in 100 cc. PhMe and the mixture heated 2 hrs., gives 80% 4-(3-diethylaminopropylamino)-2,6-bis(benzyloxy)pyrimidine (VI), m. 68° (dipicrate, m. 156°); crude VI in AcOH, hydrogenated over Pd-charcoal at room temperature and atm. pressure (4 hrs.), gives 4-(3-diethylaminopropylamino)-2,6-dihydroxypyrimidine (VII), apparently with 3 mols. AcOH, very hygroscopic; picrolonate m. 186° (decomposition); 1 of the 2 mols. of H₂O is lost at 100° and the 2nd at 130°. VII and p-ClC₆H₄N₂Cl give 57% of the 5-(p-chlorophenylazo) derivative, with 2 mols. H₂O (1 lost at 100°), yellow, m. 151° (decomposition) (dipicrate, m. 205° (decomposition)); catalytic reduction over RaneyNi gives a product rapidly oxidized in the air. Although VII was devoid of antimalarial activity, the 5-Me analog was also prepared but it was also inactive. 2,4,6-Trichloro-5-methylpyrimidine (19.7 g.) in 100 cc. Me₂CO, cautiously treated with 13 g. Et₂N(CH₂)₃NH₂ in 100 cc. Me₂CO and cooled to 4°, gives 60% of the HCl salt (VIII), m. 193-5°, of 2,6-dichloro-4-(3-diethylaminopropylamino)-5-methylpyrimidine, whose picrate m. 163°. VIII and PhCH₂ONa give the 2,6-bis(benzyloxy) derivative (IX), an oil (tripicrate, m. 141-2°). Hydrogenation of IX in AcOH over Pd-charcoal at room temperature and atm. pressure gives 7.2 g. 4-(3-diethylaminopropylamino)-2,6-dihydroxy-5-methylpyrimidine, as the triacetate (with 1 mol. H₂O); dipicrate, yellow, m. 183-4° (decomposition); picrolonate, yellow, m. 223° (decomposition). 4,6-Dichloro-2-methylaminopyrimidine (X) (4.4 g.) and PhCH₂ONa (from 1.15 g. Na) in 150 cc. PhMe, heated 1 hr. at 100°, give 27.5% 4-chloro-2-methylamino-6-(benzyloxy)pyrimidine, m. 120°; if the reaction mixture is refluxed 4 hrs., there results 61% 2-methylamino-4,6-bis(benzyloxy)pyrimidine, m. 101°; reduction (8 hrs.) in AcOH over Pd-charcoal gives 66.6% 2-methylamino-4,6-dihydroxypyrimidine (XI), with 0.5 mol. EtOH and 2/3 mols. H₂O, m. above 310°. 2,6-Dichloro-4-methylaminopyrimidine (6 g.) and PhCH₂ONa in 75 cc. PhMe, refluxed 3 hrs., give 69% 4-methylamino-2,6-bis(benzyloxy)pyrimidine, m. 118°; reduction (2.5 hrs.) in AcOH gives 98.8% 4-methylamino-2,6-dihydroxypyrimidine (XIA), m. 302° (decomposition). IV (15 g.) and 27 cc. 33% Me₂NH in 75 cc. EtOH give 48% 2,6-dichloro-4-dimethylaminopyrimidine (XII), m. 113°; with PhCH₂ONa in PhMe (refluxed 1 hr.), there results 69.5% 4-dimethylamino-2,6-bis(benzyloxy)pyrimidine, m. 79°; catalytic reduction gives 77% 4-dimethylamino-2,6-dihydroxypyrimidine, m. 320° (decomposition). The alc. mother liquor from XII yields 35% 4,6-dichloro-2-dimethylaminopyrimidine (XIII), m. 102-3°. XIII (3.5 g.) and PhCH₂ONa (from 0.84 g. Na) in 50 cc. PhMe, heated 1 hr. at 100°, give 73% 4-chloro-2-dimethylamino-6-(benzyloxy)pyrimidine, m. 84°; when refluxed 3 hrs., there results 69.5% 2-dimethylamino-4,6-bis(benzyloxy)pyrimidine, whose picrate, yellow, m. 176°; catalytic reduction gives 73% 2-dimethylamino-4,6-dihydroxypyrimidine, yellow, m. 320° (decomposition). IV (5.75 g.) in 90 cc. Me₂CO and the NH:C(NH₂)₂ from 6 g. of the HCl salt in 10 cc. H₂O, on standing 15 min., give 53% 2,6-dichloro-4-guanidinopyrimidine, m. 325° (decomposition); the mother liquor apparently contains an addnl. 43%; PhCH₂ONa in PhMe, heated 2 hrs. at 100°, gives 61% 6-chloro-4-guanidino-2-(benzyloxy)pyrimidine, m. 170° (picrate, yellow, m. 250° (decomposition)); refluxed in PhMe 8 hrs., there results 78% 4-guanidino-2,6-bis(benzyloxy)pyrimidine, characterized as the picrate, m. 200°; reduction yields 38% 4-guanidino-2,6-dihydroxypyrimidine (XIV), m. 300°. Malonylguanidine, CH:C(OH).N:C(NH₂).N:C(OH), (2 g.) and 3 g. o-H₂NC₆H₄CHO in 100 cc. H₂O containing 5 cc. HCl, heated 1 hr. on the steam bath, give 69.5% 3-amino-1-hydroxy-2,4-diazaacridine, analyzed as the HCl salt (with 2 mols. H₂O), m. above 310°; the free base, m. above 310°, gives a pale yellow solution in NaOH with a strong greenish blue fluorescence. 4-Amino-2,6-dihydroxypyrimidine and o-H₂NC₆H₄CHO give 61% 1,3-dihydroxy-2,4-diazaacridine (XV) (cf. Conrad and Reinbach, loc. cit.), which crystallizes with 1 mol. AcOH. 2,4-Diamino-6-hydroxypyrimidine (3 g.) in 100 cc. H₂O and 10 cc. AcOH, treated with 3 g. o-H₂NC₆H₄CHO in 10 cc. EtOH and refluxed 30 min., gives 35% (XVI) with 0.5 mol. H₂O, bright yellow, m. above 330°; its solutions exhibit a vivid blue fluorescence; HCl salt, biscuit-colored, m. above 310°. XI and o-H₂NC₆H₄CHO give 63.5% 3-methylamino-1-hydroxy-2,4-diazaacridine, with 4/3 mols. H₂O, pale yellow, m. above 310°; its solutions have a marked green-blue fluorescence; XIA gives XV. XIV gives 81% of the 1-guanidino analog of XV, m. above 310°; di-HCl salt, with 1.5 mols. H₂O, m. above 310°; at 120° it forms the mono-HCl salt, with 1 mol. H₂O; picrate, yellow, with 1.5 mols. H₂O, m. 230° (decomposition). The 3-(3-diethylaminopropylamino) analog of XV, obtained as a reddish oil, analyzed as the meconate (50% yield), with 5 mols. H₂O (2.5 mols. lost at 100°), pale yellow, m. 180° (decomposition); the picrate, with 1 mol. EtOH, m. 222° (decomposition) and could not be further purified. Barbituric acid (3.9 g.) and 3.9 g. 2,4-(O₂N)₂C₆H₃CHO in 150 cc. boiling H₂O give 71.5 g. of the 2,4-dinitrobenzylidene derivative, orange, m. above 310°; 2,4-H₂N(O₂N)C₆H₃CHO in dilute EtOH gives 64.5% 6-nitro-1,3-dihydroxy-2,4-diazaacridine, with 1 mol. EtOH, cream, m. above 310°; it forms an orange Na salt; in AcOH, it shows a blue fluorescence; the NO₂ group could not be reduced. These compounds were only slightly active or inactive when tested in vitro against Staphylococcus aureus.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Jansa, Petr’s team published research in Tetrahedron in 68 | CAS: 56-05-3

Tetrahedron published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, Recommanded Product: 2-Amino-4,6-dichloropyrimidine.

Jansa, Petr published the artcileAn efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids, Recommanded Product: 2-Amino-4,6-dichloropyrimidine, the publication is Tetrahedron (2012), 68(3), 865-871, database is CAplus and MEDLINE.

Polysubstituted pyrimidinylphosphonic and 1,3,5-triazinylphosphonic acids with potential biol. properties were prepared in high yields by the microwave-assisted Michaelis-Arbuzov reaction of trialkyl phosphite with the corresponding halopyrimidines and halo-1,3,5-triazines, resp., followed by the standard deprotection of the phosphonate group using TMSBr in acetonitrile. 4,6-Diamino-5-chloropyrimidin-2-ylphosphonic acid was found to exhibit a weak to moderate anti-influenza activity (28-50 μM) and may represent a novel hit for further SAR studies and antiviral improvement.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Motloch, Petr’s team published research in Organic & Biomolecular Chemistry in 18 | CAS: 56-05-3

Organic & Biomolecular Chemistry published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, Application of 2-Amino-4,6-dichloropyrimidine.

Motloch, Petr published the artcileQuantification of cooperativity in the self-assembly of H-bonded rosettes, Application of 2-Amino-4,6-dichloropyrimidine, the publication is Organic & Biomolecular Chemistry (2020), 18(8), 1602-1606, database is CAplus and MEDLINE.

The self-assembly of triaminopyrimidines with barbiturates and with cyanates was investigated in chloroform solution Equimolar mixtures of two complementary components form stable macrocyclic 3 : 3 complexes (rosettes). The thermodn. of self-assembly were quantified by using ¹H NMR titrations to measure the strength of pairwise H-bonding interactions between two rosette components (K), allosteric cooperativity associated with formation of a second H-bonding interaction with each component, and the effective molarity for cyclisation of the rosette motif (EM). Pyrimidine-cyanurate interactions are an order of magnitude more favorable than pyrimidine-barbiturate interactions, so the cyanurate rosettes are significantly more stable than barbiturate rosettes. There is no allosteric cooperativity associated with rosette formation, but the chelate cooperativity quantified by the product K EM is exceptionally high (10²-10⁴), indicating that there are no other species present that compete with rosette assembly. The values of EM for rosette formation are approx. 2 M for all four rosettes studied and are not affected by differences in peripheral substituents or intrinsic H-bond strength.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Khan, Khalid Mohammed’s team published research in Tetrahedron Letters in 56 | CAS: 56-05-3

Tetrahedron Letters published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, Formula: C4H3Cl2N3.

Khan, Khalid Mohammed published the artcileAn efficient and simple methodology for the synthesis of 2-amino-4-(N-alkyl/arylamino)-6-chloropyrimidines, Formula: C4H3Cl2N3, the publication is Tetrahedron Letters (2015), 56(10), 1179-1182, database is CAplus.

In this study, twenty-nine 2-aminopyrimidine derivatives are synthesized in good to excellent yields by fusing 2-amino-4,6-dichloropyrimidine with different amines in the presence of triethylamine without using any solvent or catalyst. Nucleophilic substitution reactions of 2-amino-4,6-dichloropyrimidine with amines were performed in ethanol. Comparisons of the yields and reaction times for both solvent and solvent-free conditions have shown that the newly developed solvent-free protocol is high yielding, more efficient, and simpler compared to conventional methods.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Kolman, Viktor’s team published research in European Journal of Medicinal Chemistry in 156 | CAS: 56-05-3

European Journal of Medicinal Chemistry published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, Related Products of pyrimidines.

Kolman, Viktor published the artcileInfluence of the C-5 substitution in polysubstituted pyrimidines on inhibition of prostaglandin E₂ production, Related Products of pyrimidines, the publication is European Journal of Medicinal Chemistry (2018), 295-301, database is CAplus and MEDLINE.

As a part of a broader structure-activity relationship study of substituted 2-aminopyrimidines, the influence of the C-5 substitution on inhibition of prostaglandin E2 (PGE2) production was studied. Thirty compounds were prepared starting from the corresponding 2-amino-4,6-dichloropyrimidines using Suzuki cross-coupling. It was shown previously that 2-amino-4,6-dichloropyrimidines with smaller C-5 substituent (hydrogen and methyl) were devoid of significant activity, while 5-Bu derivatives exhibited prominent potency. In this study, on the other hand, both monoaryl- and bisarylpyrimidines were potent inhibitors of PGE2 production regardless the length of the C-5 substituent (hydrogen, Me, n-butyl). Moreover, the shorter the C-5 substituent the higher potency to inhibit PGE₂ production was observed 2-Amino-4,6-diphenylpyrimidine was the best inhibitor of PGE2 production with IC₅₀ = 3 nM and no cytotoxicity. The most potent inhibitors deserve further preclin. evaluation as potential anti-inflammatory agents.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Kaczanowska, Katarzyna’s team published research in Proceedings of the National Academy of Sciences of the United States of America in 111 | CAS: 56-05-3

Proceedings of the National Academy of Sciences of the United States of America published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, SDS of cas: 56-05-3.

Kaczanowska, Katarzyna published the artcileStructural basis for cooperative interactions of substituted 2-aminopyrimidines with the acetylcholine binding protein, SDS of cas: 56-05-3, the publication is Proceedings of the National Academy of Sciences of the United States of America (2014), 111(29), 10749-10754, database is CAplus and MEDLINE.

The nicotinic acetylcholine receptor (nAChR) and the acetylcholine binding protein (AChBP) are pentameric oligomers in which binding sites for nicotinic agonists and competitive antagonists are found at selected subunit interfaces. The nAChR spontaneously exists in multiple conformations associated with its activation and desensitization steps, and conformations are selectively stabilized by binding of agonists and antagonists. In the nAChR, agonist binding and the associated conformational changes accompanying activation and desensitization are cooperative. AChBP, which lacks the transmembrane spanning and cytoplasmic domains, serves as a homol. model of the extracellular domain of the nAChRs. We identified unique cooperative binding behavior of a number of 4,6-disubstituted 2-aminopyrimidines to Lymnaea AChBP, with different mol. variants exhibiting pos., nH > 1.0, and neg. cooperativity, nH < 1.0. Therefore, for a distinctive set of ligands, the extracellular domain of a nAChR surrogate suffices to accommodate cooperative interactions. X-ray crystal structures of AChBP complexes with examples of each allowed the identification of structural features in the ligands that confer differences in cooperative behavior. Both sets of mols. bind at the agonist-antagonist site, as expected from their competition with epibatidine. An anal. of AChBP quaternary structure shows that cooperative ligand binding is associated with a blooming or flare conformation, a structural change not observed with the classical, noncooperative, nicotinic ligands. Pos. and neg. cooperative ligands exhibited unique features in the detailed binding determinants and poses of the complexes.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Latham, Jonathan’s team published research in Nature Communications in 7 | CAS: 5738-14-7

Nature Communications published new progress about 5738-14-7. 5738-14-7 belongs to pyrimidines, auxiliary class Pyrimidine,Amine,Alcohol,Pyrimidine, name is 2-(Dimethylamino)pyrimidine-4,6-diol, and the molecular formula is C6H9N3O2, Recommanded Product: 2-(Dimethylamino)pyrimidine-4,6-diol.

Latham, Jonathan published the artcileIntegrated catalysis opens new arylation pathways via regiodivergent enzymatic C-H activation, Recommanded Product: 2-(Dimethylamino)pyrimidine-4,6-diol, the publication is Nature Communications (2016), 11873pp., database is CAplus and MEDLINE.

The integration of regioselective halogenase enzymes with Pd-catalyzed cross-coupling chem., in one-pot reactions, successfully addresses this problem for the indole heterocycle was demonstrated. The resultant ‘chemobio-transformation’ delivered a range of functionally diverse arylated products that were impossible to access using sep. enzymic or chemocatalytic C-H activation, under mild, aqueous conditions. This use of different biocatalysts to select different C-H positions contrasts with the prevailing substrate-control approach to the area, and presented opportunities for new pathways in C-H activation chem. The issues of enzyme and transition metal compatibility were overcome through membrane compartmentalization, with the optimized process requiring no intermediate work-up or purification steps.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Schleper, A. Lennart’s team published research in Journal of Materials Chemistry C: Materials for Optical and Electronic Devices in 10 | CAS: 56-05-3

Journal of Materials Chemistry C: Materials for Optical and Electronic Devices published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, Product Details of C4H3Cl2N3.

Schleper, A. Lennart published the artcileInfluence of regioisomerism in bis(terpyridine) based exciplexes with delayed fluorescence, Product Details of C4H3Cl2N3, the publication is Journal of Materials Chemistry C: Materials for Optical and Electronic Devices (2022), 10(19), 7699-7706, database is CAplus.

Exciplexes of individual electron donor and acceptor mols. are a promising approach to utilizing otherwise non-emissive triplet states in optoelectronic applications. In this work, we synthesize a series of bis(terpyridine) pyrimidine (BTP) isomers and employ them as electron acceptors in complexes with tris(4-carbazoyl-9-ylphenyl)amine (TCTA). We show that these TCTA : BTP complexes produce thermally activated delayed fluorescence (TADF) by exciplex emission, and we investigate the influence of the nitrogen position in the pyridine on the optical and electronic properties of the exciplex. The mol. arrangement of the complex is studied using scanning tunneling microscopy (STM) as well as classical force field and d. functional theory (DFT) simulations. Finally, we fabricate organic light-emitting diodes (OLEDs) with maximum external quantum efficiencies ranging between 0.5% and 2% – depending on the BTP isomer.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Jansa, Petr’s team published research in Medicinal Chemistry Research in 24 | CAS: 56-05-3

Medicinal Chemistry Research published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, Formula: C4H3Cl2N3.

Jansa, Petr published the artcileSynthesis and structure-activity relationship studies of polysubstituted pyrimidines as inhibitors of immune-activated nitric oxide production, Formula: C4H3Cl2N3, the publication is Medicinal Chemistry Research (2015), 24(5), 2154-2166, database is CAplus.

Based on the previous discovery of the inhibitory effect of the 5-substituted 2-amino-4,6-dichloropyrimidines on nitric oxide (NO) production in vitro, a series of novel pyrimidine derivatives, namely 4,6-dichloro-2-[(N,N-dimethylamino)methyleneamino]pyrimidines, 2,4-diamino-6-chloropyrimidines, and 2,4-diamino-6-(2-hydroxyethoxy)pyrimidines, were prepared bearing various substituents at the C-5 position on the pyrimidine, such as hydrogen, Me, Et, Pr, iso-Pr, propargyl, allyl, Bu, sec-Bu, Ph, benzyl, and fluorine. The intrinsic biol. potential of the prepared compounds was characterized by effects on the in vitro production of immune-activated NO in mouse peritoneal cells. All 5-substituted 4,6-dichloro-2-[(N,N-dimethylamino)methyleneamino]pyrimidines strongly inhibited NO production The IC₅₀s were <5 μM in most cases. The highest inhibitory activity was observed for the 5-s-Bu analog (IC₅₀ = 2.57 μM), the lowest one for 5-unsubstituted compound (IC₅₀ = 11.49 μM). With the exception of the 5-fluoro-4,6-dichloro-2-[(N,N-dimethylamino)methyleneamino] derivative, all other compounds were devoid of cytotoxic effects. The hitherto obtained data suggest that the NO-inhibitory activity depends on the presence of the 2-amino-4,6-dichloropyrimidine scaffold.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Jansa, Petr’s team published research in Medicinal Chemistry Research in 23 | CAS: 56-05-3

Jansa, Petr published the artcile5-Substituted 2-amino-4,6-dihydroxypyrimidines and 2-amino-4,6-dichloropyrimidines. Synthesis and inhibitory effects on immune-activated nitric oxide production, Application In Synthesis of 56-05-3, the publication is Medicinal Chemistry Research (2014), 23(10), 4482-4490, database is CAplus and MEDLINE.

A series of 5-substituted 2-amino-4,6-dihydroxypyrimidines were prepared by a modified condensation of the corresponding monosubstituted malonic acid diesters with guanidine in an excess of sodium ethoxide. The optimized procedure using Vilsmeier-Haack-Arnold reagent, followed by immediate deprotection of the (dimethylamino)methylene protecting groups, was developed to convert the 2-amino-4,6-dihydroxypyrimidine analogs to novel 5-substituted 2-amino-4,6-dichloropyrimidines in high yields. Pilot screening for biol. properties of the prepared compounds was done in mouse peritoneal cells using the in vitro nitric oxide (NO) assay. Irresp. of the substituent at the 5 position, 2-amino-4,6-dichloropyrimidines inhibited immune-activated NO production The most effective was 5-fluoro-2-amino-4,6-dichloropyrimidine with an IC₅₀ of 2 μM (higher activity than the most potent reference compound) while the IC₅₀s of other derivatives were within the range of 9-36 μM. The 2-amino-4,6-dihydroxypyrimidine counterparts were devoid of any NO-inhibitory activity. The compounds had no suppressive effects on the viability of cells.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia