Category: 54385-49-8

Taylor, Edward C. published the artcile3-Cyano-4-aminopyrazolo[3,4-d]pyrimidine, an azalog of the aglycone of toyocamycin, SDS of cas: 54385-49-8, the main research area is .

cf. CA 63, 602a. Condensation of (NC)2C:C(CN)2 with H2NC(:NH)NH2.HCl followed by hydrolysis gave a good yield of 5-aminopyrazole-3,4-dicarbonitrile (I, R = NH2) (II). Reaction of II with HC(OEt)3 under anhydrous conditions by refluxing 7 h., isolation of the intermediate I (R = N:CHOEt) (III), and treatment with alc. NH3 gave 83% yield of the desired aglycon analog (IV, R = CN) (V). III recrystallized from C5H5N-petroleum ether without special precautions against moisture gave I (R = NHCHO). V refluxed 24 h. in 10% aqueous NaOH and acidified with 9% aqueous HCl gave the acid IV (R = CO2H), sublimed in vacuo to 4-aminopyrazolo[3,4-d] pyrimidine IV (R = H). V in 8% aqueous HCl stirred at 0° with addition of aqueous NaNO2, the mixture boiled and the isolated product recrystallized gave 3-cyano-4(5H)-pyrazolo[3,4-d]pyrimidinone.

Journal of Organic Chemistry published new progress in CAplus about 54385-49-8, 54385-49-8 belongs to class pyrazoles-derivatives, name is 5-Amino-1H-pyrazole-3,4-dicarbonitrile, and the molecular formula is C5H3N5, SDS of cas: 54385-49-8.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Shakir, Mohammed published the artcile3,4-Dicyano-5-aminopyrazole complexes of anhydrous divalent transition metal chlorides and their triphenylphosphine derivatives, Synthetic Route of 54385-49-8, the main research area is transition metal aminocyanopyrazole complex; pyrazole dicyanoamino transition metal complex; cyanoaminopyrazole transition metal complex.

3,4-Dicyano-5-aminopyrazole (L) reacts either with anhydrous MCl2 or with [M(PPh3)2Cl2] to yield ML4Cl2 (M = Cr, Mn, Fe, Co, Ni, Cu, Zn, Cd, Hg), whose monomeric and covalent natures were confirmed by their solubility in most nonpolar solvents and their low elec. conductivities. The bonding mode of substituted pyrazole is inferred from the position of the ν(C:N) band in the IR spectra. The electronic spectra and the magnetic moments of these compounds were recorded.

Transition Metal Chemistry (Dordrecht, Netherlands) published new progress about transition metal aminocyanopyrazole complex; pyrazole dicyanoamino transition metal complex; cyanoaminopyrazole transition metal complex. 54385-49-8 belongs to class pyrazoles-derivatives, name is 5-Amino-1H-pyrazole-3,4-dicarbonitrile, and the molecular formula is C5H3N5, Synthetic Route of 54385-49-8.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Hecht, Sidney M. published the artcileStructure determination of the N-methyl isomers of 5-amino-3,4-dicyanopyrazole and certain related pyrazolo[3,4-d]pyrimidines, Recommanded Product: 5-Amino-1H-pyrazole-3,4-dicarbonitrile, the main research area is pyrazoledicarbonitrile amino tautomerism; tautomerism aminopyrazoledicarbonitrile; pyrazolopyrimidine structure.

Addnl. data considered in abstracting and indexing are available from a source cited in the original document. The position of N substitution of 4-aminopyrazolo[3, 4-d]pyrimidine derivatives was studied by chem. and spectroscopic techniques, and structures were assigned to the pyrazole precursors of these compounds The more abundant pyrazole resulting from treatment of tetracyanoethylene with MeNHNH2 was 3-amino-4, 5-dicyano-1-methylpyrazole (I) on the basis of its conversion to a pyrazolo[3,4-d]pyrimidine identical with authentic 4-amino-2-methylpyrazolo[3,4-d]pyrimidine, rather than with the authentic 1-methyl isomer. The assigned structure was verified by x-ray crystallog. determination of I. Because I was not expected to be the more abundant pyrazole, a mechanism was proposed to account for its formation. 13C NMR and uv data for 3-amino-4,5-dicyanopyrazole indicated that 5-amino-3,4-dicyano-1H-pyrazole was the major tautomer.

Journal of Organic Chemistry published new progress about Tautomers. 54385-49-8 belongs to class pyrazoles-derivatives, name is 5-Amino-1H-pyrazole-3,4-dicarbonitrile, and the molecular formula is C5H3N5, Recommanded Product: 5-Amino-1H-pyrazole-3,4-dicarbonitrile.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Earl, Robert A. published the artcileChemical and carbon-13 nuclear magnetic resonance reinvestigation of the N-methyl isomers obtained by direct methylation of 5-amino-3,4-dicyanopyrazole and the synthesis of certain pyrazolo[3,4-d]pyrimidines, SDS of cas: 54385-49-8, the main research area is pyrazole amino dicyano methylation; methylation aminodicyanopyrazole; pyrazolopyrimidine amino methyl.

The structural assignments for the isomeric N-1- and N-2-methyl derivatives of 5-amino-3,4-dicyanopyrazole obtained by direct methylation by C. L. Dickenson et. al (1964) were reinvestigated. The higher melting isomer was annulated to give 4-amino-3-cyano-1-methylpyrazolo[3,4-d]pyrimidine (I, R = CN), which with alkaline peroxide gave I (R = CONH2). Hydrolysis of I (R = CONH2) under more vigorous conditions gave I (R = CO2H), which was decarboxylated in hot sulfolane to give I (R = H). This established the structure of the N-methylpyrazole as 5-amino-3,4-dicyano-1-methylpyrazole and reversed the structural assignment previously reported. A similar reaction sequence converted the lower melting isomer into 4-amino-2-methylpyrazolo[3,4-d]pyrimidine (II) and established the structure as 5-amino-3,4-dicyano-2-methylpyrazole.

Journal of Organic Chemistry published new progress about Methylation. 54385-49-8 belongs to class pyrazoles-derivatives, name is 5-Amino-1H-pyrazole-3,4-dicarbonitrile, and the molecular formula is C5H3N5, SDS of cas: 54385-49-8.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Hassan, Alaa A. published the artcilePyrazole, pyrazolo[1,2-c]-1,3,4-thiadiazole and thiadiazepine derivatives from thiosemicarbazides, COA of Formula: C5H3N5, the main research area is thiosemicarbazide tetracyanoethene cyclization; pyrazole derivative preparation; pyrazolothiadiazole derivative preparation; thiadiazepine derivative preparation.

Thiosemicarbazides RNHCSNHNH2 [R = Ph, Bn, allyl] reacted with tetracyanoethene in Et acetate with admission of air to form the 7-amino-2-organylimino-2,3-dihydro-1,3,4-thiadiazepine-5,6-dicarbonitriles I [ R = Ph, Bn], 7-amino-1-organylimino-3-oxopyrazolo[1,2-c]-1,3,4-thiadiazole-5,5,6-tricarbonitriles II, 7-amino-1-organyl-iminopyrazolo[1,2-c]-1,3,4-thiadiazole-3,3,5,5,6-pentacarbonitriles III and 3-amino-1H-pyrazole-4,5-dicarbonitrile (IV) in moderate yields. Rationales for the observed conversations are presented.

ARKIVOC (Gainesville, FL, United States) published new progress about Cyclization. 54385-49-8 belongs to class pyrazoles-derivatives, name is 5-Amino-1H-pyrazole-3,4-dicarbonitrile, and the molecular formula is C5H3N5, COA of Formula: C5H3N5.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Hecht, Sidney M. published the artcileActivation of cytokinins, Quality Control of 54385-49-8, the main research area is cytokinin analog structure activity; plant hormone cytokinin analog.

A number of cytokinin analogs containing modifications in the heterocyclic moiety were prepared These compounds were tested for activity as cytokinins and anticytokinins in the tobacco bioassay and the results were used to determine whether any position(s) of the heterocyclic nucleus of cytokinins may require derivatization as part of an over-all activation process. 3-Substituted 4-alkylaminopyrazolo[3,4-d]pyrimidines and 4-alkylaminopyrrolo[2,3-d]pyrimidines, have carbon rather than nitrogen atoms at positions 3 and 5, resp., (analogous to position 7 in purines) and would be predicted to be metabolically stable at these positions. The finding that these compounds had cytokinin activity suggested that modification at the metabolically stable position, and by extension at position 7 in cytokinin analogs which are purines, is not a prerequisite for the expression of cytokinin activity. Similar consideration of other heterocyclic analogs which have cytokinin activity suggests that the active form of a cytokinin can be the exogenous compound itself. Certain structural analogs of cytokinins were found to inhibit the growth of tobacco callus promoted by 6-(3-methyl-2-butenylamino)purine. These compounds were studied as potential cytokinin antagonists, i.e. having activity analogous to the 7-alkylamino-3-methylpyrazolo[4,3-d]pyrimidines (Hecht, S. M., Bock, R. M., Schmitz, R. Y., Skoog, F., and Leonard, N. J. 1971; Skoog, F., Schmitz, R. Y., Hecht, S. M., and Bock, R. M. 1973). The activity of these compounds is discussed and criteria are proposed to distinguish between those species which are specific anticytokinins and those which otherwise inhibit growth.

Journal of Biological Chemistry published new progress about Structure-activity relationship. 54385-49-8 belongs to class pyrazoles-derivatives, name is 5-Amino-1H-pyrazole-3,4-dicarbonitrile, and the molecular formula is C5H3N5, Quality Control of 54385-49-8.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 54385-49-8, 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. 54385-49-8 name is 5-Amino-1H-pyrazole-3,4-dicarbonitrile, This 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.

5-Amino-lH-pyrazole-3,4-dicarbonitrile (7.6 g, 57 mmol) was suspended in trimethylorthoformate (60 mL) in a round bottom flask fitted with a stirbar and reflux condenser. The flask was placed in an oil bath and the mixture was heated at reflux overnight. After cooling to rt the following morning, the reaction solution was concentrated under reduced pressure to afford an orange oil. The oil was dried under high vacuum with stirring for 2h. The residue was dissolved in MeOH (25 mL) and cooled under nitrogen in an ice-water bath. A solution of ammonia in MeOH (7.0 M, 65 mL, 460 mmol) was added. The resulting slightly opaque solution was warmed to rt and stirred overnight. The solids produced were isolated by suction filtration, washed with MeOH and dried under suction. The tan powder was transferred to a round bottom flask and dried under high vacuum and used without further purification (6.20 g, 68%, 2 steps). LCMS (AA): m/z 161 (M+H); 1H MR (300 MHz, i-DMSO) delta 8.04 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Amino-1H-pyrazole-3,4-dicarbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; ADHIKARI, Sharmila; CALDERWOOD, Emily, Frances; ENGLAND, Dylan, Bradley; GOULD, Alexandra, E.; HARRISON, Sean, J.; HUANG, Shih-Chung; MA, Liting; (316 pag.)WO2018/89786; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics