Category: 69205-79-4

Electric Literature of 69205-79-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 69205-79-4, name is 2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile, molecular formula is C7H5N5O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

In a dry round bottomed flask under an atmosphere of argon, trityl chloride (1.20 g, 4.28 mmol) was added to a solution of 2-amino-4,7-dihydro-4-oxo-3A/- pyrrolo[2,3-d]pyrimidine-5-carbonitrile (0.50 g, 2.85 mmol) in dry pyridine (29 ml_). The mixture reaction was heated at 90 C for 48 h. The reaction mixture was concentrated under reduced pressure then absorbed on silica gel and purified by flash chromatography on silica gel eluting with dichloromethane/MeOH with a gradient starting at 2% of MeOH and rising to 10%. The desired compound was obtained as a brown solid (0.63 g, 1.5 mmol, 53% yield). Procedure based on Olgen 2008. deltaEta (400 MHz, DMSO-de) delta 11.80 (br s, 1H); 10.64 (br s, 1H), 7.56 (s, 1H), 7.41(s, 1H), 7.29-7.28 (m, 12H), 7.23-7.17 (m, 3H), 5.73 (s, 1H). HRMS (m/z ESI+) : C26Hi8N50 [M-H]+ Found 416.1514 Requires: 416.1511.

According to the analysis of related databases, 69205-79-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE PROVOST, FELLOWS, FOUNDATION SCHOLARS, AND THE OTHER MEMBERS OF BOARD, OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH, NEAR DUBLIN; SOUTHERN, John, Michael; CONNON, Stephen, J.; (37 pag.)WO2016/50804; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 69205-79-4, 2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile, 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, Formula: C7H5N5O, blongs to pyrimidines compound. Formula: C7H5N5O

In a dry round bottomed flask under an atmosphere of argon, trityl chloride (1.20 g, 4.28 mmol) was added to a solution of 2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (0.50 g, 2.85 mmol) in dry pyridine (29 mL). The mixture reaction was heated at 90 C for 48 h. The reaction mixture was concentrated under reduced pressure then absorbed on silica gel and purified by flash chromatography on silica gel eluting with dichloromethane/MeOH with a gradient starting at 2% of MeOH and rising to lO%. The desired compound wasobtained as a brown solid (0.63 g, 1.5 mmol, 53% yield).Procedure based on Olgen 2008.OH (400 MHz, DMSO-d6) oe 11.80 (br s, 1H); 10.64 (br s, 1H), 7.56 (s, 1H), 7.41(s, 1H), 7.29-7.28 (m, 12H), 7.23-7.17 (m, 3H), 5.73 (s, 1H).HRMS (m/z ESI): C26H18N50 [M-H] Found 416.1514 Requires: 416.1511.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69205-79-4, 2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; THE PROVOST, FELLOWS, FOUNDATION SCHOLARS, AND THE OTHER MEMBERS OF BOARD, OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH, NEAR DUBLIN; KELLY, Vincent; (44 pag.)WO2016/50806; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 69205-79-4, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 69205-79-4 as follows.

Anew synthesis of 7-formyl-preQ0 (systematic name, 2-amino-5-formylpyrrolo[2,3-d]pyrimidin-4-one) that, contrary to literature-known procedures (21-23), does not require protecting group chemistry was developed. PreQ0 (808 mg, 4.61 mmol)and sodium hypophosphite dihydrate (1.44 g, 13.6 mmol) were dissolved in the solvent mixture (15 ml of pyridine/acetic acid/deionized water in a ratio of 2:1:1) and stirred under inert atmosphere.Raney nickel catalyst (slurry in water, 500 mg) wasadded to the stirred reaction mixture. Safety precaution: dryRaney nickel is pyrophoric and should always be handled underinert atmosphere. The resulting reaction mixture was heated to50 C for 5 h. Subsequently, the reaction mixture was cooled to room temperature and filtered over a pad of celite. The filtrate was reduced in vacuo. The remaining brown residue was dissolvedin 6 M aqueous potassium hydroxide solution. The remaining solids were filtered off. The filtrate was cooled to 0 Cand neutralized by addition of concentrated aqueous HCl. Theproduct precipitated from the solution and was isolated by filtrationand washed with copious amounts of ice water and acetone(brown solid, 770 mg, 94%). 1H NMR (DMSO-d6) 6.35(bs, 2H, NH2), 7.49 (s, 1H, H-8), 10.04 (s, 1H, CHO), 10.72 (bs,1H, H-9), 11.96 (bs, 1H, H-1); 13C NMR (DMSO-d6) 98.36(C-7), 120.34 (C-8), 124.50 (C-5), 153.40 (C-2), 153.83 (C-4),159.02 (C-6), 185.47 (CHO). NMR data were recorded on aBruker AVANCE III with autosampler (1H NMR 300.36 MHz,13C NMR 75.53 MHz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69205-79-4, its application will become more common.

Reference:
Article; Jung, Jihye; Czabany, Tibor; Wilding, Birgit; Klempier, Norbert; Nidetzky, Bernd; Journal of Biological Chemistry; vol. 291; 49; (2016); p. 25411 – 25426;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia