23956-12-9 | Pyrimidines

Simple exploration of 23956-12-9

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 23956-12-9, 5-(2-Hydroxyethyl)pyrimidine-2,4(1H,3H)-dione, other downstream synthetic routes, hurry up and to see.

Electric Literature of 23956-12-9 ,Some common heterocyclic compound, 23956-12-9, molecular formula is C6H8N2O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: To a solution of dry 2 (140 mg, 0.897 mmol) and K2CO3 (619.6 mg, 4.48 mmol) in anhydrous DMF (10 mL) at 15 C MOMCl (0.27 mL, 3.56 mmol) was added. Reaction mixture was stirred at r.t. overnight. Solvent was evaporated in vacuo and residue was purified by column chromatography (CH2Cl2 : MeOH = 20 : 1) to yield white powder of 12a (42.7 mg, 23.8 %, m.p. = 124126 C), colorless oil of 12b (26.5 mg, 14.8 %) and white powder of 12c (5.4 mg, 2.5 %, m.p. = 9294 C). 12a: 1H-NMR: 11.01 (1H, s, NH-3), 7.29 (1H, s, H-6), 5.17 (2H, s, CH2-N1), 4.55 (1H, t, J = 5.30 Hz, OH), 3.47 (2H, q, J = 6.14 Hz, H-2′), 3.27 (3H, s, OCH3-N1), 2.36 (2H, t, J = 6.54 Hz, H-1′). 13C-NMR: 164.43 (C-4), 151.49 (C-2), 142.04 (C-6), 111.00 (C-5), 77.93 (CH2-N1), 59.73 (C-2′), 56.45 (OCH3-N1), 30.27 (C-1′). ESI-MS 201 [M+H]+. Anal. calcd. For C8H12N2O4: C 48.00, H 6.04. Found: C 47.94, H 6.06. 12b: 1H-NMR: 10.81 (1H, s, NH-1), 7.54 (1H, s, H-6), 5.26 (2H, s, CH2-N3), 4.48 (1H, t, J = 5.62 Hz, OH), 3.53 (2H, t, J = 6.20 Hz, H-2′), 3.22 (3H, s, OCH3-N3), 2.38 (2H, t, J = 6.55 Hz, H-1′). 13C-NMR: 164.92 (C-4), 151.78 (C-2), 139.46 (C-6), 109.11 (C-5), 65.93 (CH2-N3), 59.69 (C-2′), 55.04 (OCH3-N3), 26.99 (C-1′). ESI-MS 201 [M+H]+. Anal. calcd. For C8H12N2O4: C, 48.00; H, 6.04. Found: C 48.07, H 6.06. 12c: 1H-NMR: 7.63 (1H, s, H-6), 5.21 (2H, s, CH2-N1), 5.08 (2H, s, CH2-N3), 4.60 (1H, t, J = 5.49 Hz, OH), 3.29 (3H, s, OCH3-N1), 3.28 (3H, s, OCH3-N3), 3.51 (2H, q, J = 6.16 Hz, H-2′), 2.40 (2H, t, J = 6.51 Hz, H-1′). 13C-NMR: 164.23 (C-4), 151.72 (C-2), 141.55 (C-6), 110.21 (C-5), 79.11 (CH2-N1), 71.99 (CH2-N3), 59.56 (C-2′), 57.38 (OCH3-N1), 56.64 (OCH3-N3), 30.79 (C-1′). ESI-MS 245 [M+H]+. Anal. calcd. For C10H16N2O5: C 49.17, H 6.60. Found: C 49.09, H 6.59.

Reference:
Article; Kraljevi?, Tatjana Gazivoda; Klika, Mateja; Kralj, Marijeta; Martin-Kleiner, Irena; Jurmanovi?, Stella; Mili?, Astrid; Padovan, Jasna; Rai?-Mali?, Silvana; Bioorganic and Medicinal Chemistry Letters; vol. 22; 1; (2012); p. 308 – 312;,
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The origin of a common compound about 5-(2-Hydroxyethyl)pyrimidine-2,4(1H,3H)-dione

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 23956-12-9, 5-(2-Hydroxyethyl)pyrimidine-2,4(1H,3H)-dione.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 23956-12-9, name is 5-(2-Hydroxyethyl)pyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below., Formula: C6H8N2O3

On the basis of the modification of the 5-position of the uracil. The preparation of hydroxyethyluracil 28 is possible on a large scale according to a known method (J. D. Fissekis, A. Myles, G. B. Brown, J. Org. Chem. 1964, 29, 2670. g-Butyrolactone 25 was formylated with methyl formate, the sodium salt 26 was reacted to give the urea derivative 27 and this was cyclized to the hydroxyethyluracil 28 (Scheme 1). [C00006] [C00007] [00083] Hydroxyethyluracil 28 was methylated with methanesulphonyl chloride in pyridine to give 29 (J. D. Fissekis, F. Sweet, J. Org. Chem. 1973, 38, 264). [00084] The following stages have been newly invented: using sodium azide in DMF, 29 was reacted to give the azide 30 and this was reduced with triphenylphosphine in pyridine to give the aminoethyluracil 31. The amino function in 31 was finally protected with N-ethoxycarbonylphtalimide (Scheme 2). Nucleosidation of ribose tetrabenzoate 33 with N-phtaloylaminoethyluracil 32 produced the ribose tribenzoate 34 in good yields. The anomeric centre of the pyranose ring is in the beta configuration, as can be clearly seen from the coupling constants between H-C(1′) and H-C(2′) of J=9.5 Hz. Subsequent removal of the benzoate protective groups using NaOMe in MeOH yielded the linker triol 35. 35 was reacted with benzoyl chloride at -78 C. in pyridine/dichlormethane 1:10 in the presence of DMAP. In this process, in addition to the desired 2′-benzoate 36 (64%), 2′,4′-dibenzoylated product (22%) was also obtained, which was collected and converted into the triol 35 analogously to the methanolysis of 34 to 35. The 2′-benzoate 36 was tritylated with dimethoxytrityl chloride in the 4′-position in yields of greater than 90% in the presence of Huenig’s base in dichloromethane. The rearrangement of 4′-DMT-2′-benzoate 37 to the 4′-DMT-3′-benzoate 38 was carried out in the presence of DMAP, p-nitrophenol and Huenig’s base in n-propanol/pyridine 5:2. After chromatography, 38 is obtained. 4′-DMT-3′-benzoate 38 was finally reacted with ClP (OAll)N(iPr)2 to give the phosphoramidite 39 in the presence of Hunig’s base (Scheme 3). This can be employed for the automated oligonucleotide synthesis without alteration of the synthesis protocols.

Reference:
Patent; Nanogen Recognomics GmbH; US6699978; (2004); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Analyzing the synthesis route of 5-(2-Hydroxyethyl)pyrimidine-2,4(1H,3H)-dione

Related Products of 23956-12-9, Adding some certain compound to certain chemical reactions, such as: 23956-12-9, name is 5-(2-Hydroxyethyl)pyrimidine-2,4(1H,3H)-dione,molecular formula is C6H8N2O3, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 23956-12-9.

Mixture of 2 (2.75 g, 17.61 mmol) and acetic anhydride (14.1 mL, 0.15 mol) in anhydrous pyridine (25 mL) was refluxed for 1 h, then water (20 mL) was added and solvent was removed under reduced pressure. Co-evaporation of oily residue with toluene (2 x 30 mL) gave crude product which was purified by column chromatography (CH2Cl2 : CH3OH = 20 :1) to give white crystals of 4 (3.31 g, 95 %, m.p.= 205 – 207 C). 1H-NMR: 11.08 (1H, s, NH-3), 10.72 (1H, s, NH-1), 7.32 (1H, s, H-6), 4.07 (2H, t, J = 6.73 Hz, H-2′), 2.48 (2H, t, J = 6.69 Hz, H-1′), 1.99 (3H, s, CH3). 13C-NMR: 170.72 (C=O), 159.60 (C-4), 156.13 (C-2), 151.28 (C-6), 115.17 (C-5), 62.75 (C-2′), 24.32 (C-1′), 21.13 (CH3). ESI-MS 199 [M+H]+. Anal. calcd. For C8H10N2O4: C 48.48, H 5.09. Found: C 48.39, H 5.11.