Category: 15400-54-1

Perez, Miguel A.; Soto, Jose L. published their research in Synthesis on December 31 ,1981. The article was titled 《Synthesis of 6-alkoxy-2-amino-5-cyanopyrimidines through sodium alkoxide-induced regiospecific cyclization of 1,3-dicarbonitriles》.Formula: C7H10N4O2 The article contains the following contents:

The reaction of R1C(OR):C(CN)2 (R = Et, Me; R1 = H, Me, Ph, tolyl, anisyl, ClC6H4, O2NC6H4) with H2NCN and NaOR2-R2OH (R2 = Me, Et, Pr) yielded the resp. pyrimidinecarbonitriles I. Similarly, pyrimidines II were prepared from R1C(OR):C(CN)2, H2NC(OMe):N+H2 Cl-, and NaOMe-MeOH. A mixture of EtOCH:C(CN)2, H2NCH, and NaOMe in MeOH was refluxed to give I (R1 = H, R2 = Me). In the experiment, the researchers used many compounds, for example, Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1Formula: C7H10N4O2)

Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1) belongs to anime. Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. Aromatic amines have the nitrogen atom connected to an aromatic ring.Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine (NClH2).Formula: C7H10N4O2

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

《Synthesis and evaluation of antibacterial activity of some new N,N’-(5-(6-(4-substitutedphenyl)imidazo[2,1-b][1,3,4]-thiadiazol-2-yl)pyrimidine-2,4-diyl)diacetamide derivatives》 was published in Pharma Chemica in 2010. These research results belong to Sankangoud, Ramappa M.; Chatni, Nandini B.; Goudanavar, Prakash S.. Reference of Ethyl 2,4-diaminopyrimidine-5-carboxylate The article mentions the following:

A series of new N,N’-(5-(6-(4-substitutedphenyl)imidazo[2,1-b][1,3,4]-thiadiazol-2-yl)pyrimidine-2,4-diyl)diacetamide derivatives, e. g. I, were synthesized and tested for their antibacterial activity. Guanidine carbonate & Et (ethoxymethylene) cyanoacetate were used as the starting materials for the preparation of ethyl-2,4-diaminopyrimidine-5-carboxylate. The reactive amino groups were acetylated using acetic anhydride in presence of DMF to form Et 2,4-diacetamidopyrimidine-5-carboxylate. Efforts without masking the reactive amino groups on pyrimidine at this stage did not yield the target compounds Further Et group from position 5 was removed as ethanol by refluxing with 10% alc. NaOH for 10 min to form 2,4-diacetamidopyrimidine-5-carboxylic acid. This acid was refluxed for 4 h with thiosemicarbazide and phosphorous oxychloride to get N,N’-(5-(5-amino-1,3,4-thiadiazol-2-yl)pyrimidine-2,4-diyl)diacetamide. Further target compounds were synthesized using different substituted phenacyl bromides and their structureswere confirmed by IR and 1H NMR spectroscopy. They were tested for their antibacterial activities using cup-plate-agar-diffusion method and 3 compounds have shown potent activity against both gram-pos. and gram-neg. microorganisms as compared to the standard drug methotrexate. In the experimental materials used by the author, we found Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1Reference of Ethyl 2,4-diaminopyrimidine-5-carboxylate)

Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).Reference of Ethyl 2,4-diaminopyrimidine-5-carboxylate

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

《Pyrimidine synthesis from ethyl ethoxymethylenecyanoacetate and amidines》 was published in Tetrahedron Letters in 1969. These research results belong to Nishigaki, Sadao; Aida, Kyoko; Senga, Keitaro; Yoneda, Fumio. Synthetic Route of C7H10N4O2 The article mentions the following:

Treatment of 1 equivalent EtOH:C(CN)CO2Et(I) with 3 equivalents MeC(:NH)NH2 (II) in cold EtOH and maintaining the mixture at 0° 18 hrs. yielded 85.5% 5-cyano-4-hydroxy-2-methylpyrimidine acetamidinate (III, R = Me) (IV), m. 184-8° (EtOAc). Use of 2 or 1 equivalent II decreased the yields of IV to 69.0 and 20.3%, resp. A small amount of ethyl 4-amino-2-methyl-5-pyrimidinecarboxylate (V) was extracted from the reactions mixtures with Et2O. IV neutralized with AcOH gave 5-cyano-4-hydroxy-2-methylpyrimidine, reconverted to IV by treating with an equimolar amount of II in alc. The mass spectrum of IV revealed the strong parent ions m/e 135, 58 but no mol. ion, m/e 193, corresponding to N-(3-acetamidino-2-cyanoacryloyl)acetamidine, H2NCR:NCH:C(CN)CONHCR:-NH (VI, R = Me) (VII). The reactions of I with 2-ethyl-2-thiopseudourea (VIII) in MeOH readily gave Et 3-[[amino-(ethylthio)methylene]amino]-2-cyanoacrylate (IX); III (R = EtS) (X), m. 175-7°; and traces of V. Increase of the ratio of VIII to I from 1:1 to 4:1 led to decrease of the % yield of IX and increase of X. The reactions of guanidine with I in cold alc. gave predominantly Et 2,4-diamino-5-pyrimidinecarboxylate (XI), m. 215-17° (alc.), along with a trace of III (R = NH2) (XII), m. >300° (MeOH), converted to 2-amino-5-cyano-4-hydroxypyrimidine, m. >300° (AcOH), by treating with AcOH. Use of a large excess of guanidine increased the yield of XI to 95% in the absence of XII. After reading the article, we found that the author used Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1Synthetic Route of C7H10N4O2)

Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1) belongs to anime. Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. Aromatic amines have the nitrogen atom connected to an aromatic ring.Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine (NClH2).Synthetic Route of C7H10N4O2

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Oppenlaender, Thomas; Pfoertner, Karl Heinz; Schoenholzer, Peter published an article in Helvetica Chimica Acta. The title of the article was 《Photooxygenation of 5-aryl-2,4-diaminopyrimidines leading to 4-amino-1,3,5-triazin-2-yl ketones and, in the presence of sodium borohydride, to 5,6-dihydro-4(3H)-pyrimidinones》.Related Products of 15400-54-1 The author mentioned the following in the article:

The photosensitized oxygenation of 5-aryl-2,4-diaminopyrimidines I (R = 4-ClC6H4, Ph; R1 = Et, H Me, Ph) in protic solvents led to the formation of the new 4-amino-1,3,5-triazin-2-yl ketones II in high yields. The structures of II were elucidated by spectroscopic means, especially by 13C-NMR and UV data. Photooxygenation of I (R = 4-ClC6H4, R1 = Et) under reductive conditions, e.g. in the presence of excess of NaBH4, gave 5,6-dihydro-5-hydroxy-4(3H)-pyrimidinone III, the structure of which was determined by x-ray anal. In the proposed mechanisms for both types of reactions, a dipolar ion formed by attack of 1O2 on C5 is assumed to be a common intermediate. For the new efficient synthesis of 1,3,5-triazines from 2,4-diaminopyrimidines, a 5-aryl substituent seems to be essential. In the experiment, the researchers used many compounds, for example, Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1Related Products of 15400-54-1)

Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.Related Products of 15400-54-1

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The author of 《Protonation of 2,4-diaminopyrimidines. I. Dissociation constants and substituent effects》 were Roth, Barbara; Strelitz, Justina Z.. And the article was published in Journal of Organic Chemistry in 1969. Computed Properties of C7H10N4O2 The author mentioned the following in the article:

The basic dissociation constant of a series of approx. 70 2,4-diaminopyrimidines and condensed pyrimidine derivatives were obtained. The major effect of 5 substitution is inductive, but there is a greater resonance component than can be accounted for by correlation with Hammett σm constant The effect of 6 substitution, on the other hand, is almost completely inductive. Similar relations were found with 4-amino-6-substituted pyrimidines. In some cases H bonding renders such correlations imprecise. Dissociation constant of 4-substituted pyrimidines can be correlated with σp constant, but 2-substituted derivatives appear to have a considerately greater inductive component. The shifts in uv maximum of 2,4-diamino-6-substituted, but not 5-substituted, pyrimidines had a dependence on the + R or -R character of the substituents. Ion pair formation between certain diaminopyrimidines and divalent ions in aqueous solution was postulated on the basis of uv studies. After reading the article, we found that the author used Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1Computed Properties of C7H10N4O2)

Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).Computed Properties of C7H10N4O2

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In 1970,Chemical & Pharmaceutical Bulletin included an article by Nishigaki, Sadao; Senga, Keitaro; Aida, Kyoko; Takabatake, Toyomi; Yoneda, Fumio. Synthetic Route of C7H10N4O2. The article was titled 《Condensation reactions of ethyl ethoxymethylenecyanoacetate with amidines》. The information in the text is summarized as follows:

The pyrimidine synthesis from ethyl ethoxymethylenecyanoacetate (EMCE) and amidines is significantly influenced by the mole ratios of reacting components. In general the use of excess amidine gives better yields. Condensation of EMCE with excess acetamidine gives 4-hydroxy-2-methyl-5-pyrimidinecarbonitrile acetamidinate as the main product in good yield. Reaction between EMCE and excess 2-ethyl-2-thiopseudourea gives 2-ethylthio-4-hydroxy-5-pyrimidinecarbonitrile 2-ethyl-2-thiopseudoureate rather than 3-[3 – [[amino(ethylthio)methylene]amino] – 2 – cyanoacryloyl] – 2 – ethyl-2-thiopseudourea originally claimed. The condensation reactions of EMCE with other amidines such as guanidine and benzamidine have been studied.Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1Synthetic Route of C7H10N4O2) was used in this study.

Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1) belongs to anime. Halogenation, in which one or more hydrogen atoms of an amine is replaced by a halogen atom, occurs with chlorine, bromine, and iodine, as well as with some other reagents, notably hypochlorous acid (HClO). With primary amines the reaction proceeds in two stages, producing N-chloro- and N,N-dichloro-amines, RNHCl and RNCl2, respectively. With tertiary amines, an alkyl group may be displaced by a halogen.Synthetic Route of C7H10N4O2

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The author of 《Synthesis of pyrimido[4,5-d]pyrimidines. An unusual rearrangement of 2-aminopyrimido[4,5-d]pyrimidin-5(6H)-one into 2-amino-4,6-dichloro-1,3,5-triazine》 were Stanovnik, B.; Koren, B.; Steblaj, M.; Tisler, M.; Zmitek, J.. And the article was published in Vestnik Slovenskega Kemijskega Drustva in 1982. Electric Literature of C7H10N4O2 The author mentioned the following in the article:

Pyrimidopyrimidine I (R = NH2, R1 = H) was obtained by treating 5-carbamoyl-2,4-pyrimidinediamine (II) with HC(OEt)3 or CH(NHCHO)3. I (R = N:CMeOEt, R1 = Me) was obtained from II and MeC(OEt)3. Treatment of I (R = NH2, R1 = H) with POCl3 gave the triazine III. In the experiment, the researchers used Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1Electric Literature of C7H10N4O2)

Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1) 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.Electric Literature of C7H10N4O2

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The author of 《Pyrimidines. II. Nucleophilic substitution reactions of ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate》 were Shadbolt, Roy S.; Ulbricht, Tilo L. V.. And the article was published in Journal of the Chemical Society [Section] C: Organic in 1967. Application In Synthesis of Ethyl 2,4-diaminopyrimidine-5-carboxylate The author mentioned the following in the article:

cf. CA 56: 470b. Treatment of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (I) with dimethylamine, PhONa, PhSNa, KF, or the triethylamine salt of N-hydroxyphthalimide yielded normal substitution products. However, when the chloropyrimidine was treated with NaCN in Me2SO, or LiCN in dimethylformamide, in attempts to prepare the 4-cyano derivative, ethyl 2,4-bis(methylthio)pyridmidine-5-carboxylate was obtained. Investigation of this reaction, and of the other products, suggested that the methylthio group in ethyl-4-chloro-2-(methylthio)pyrimidine-5-carboxylate is displaced by cyanide ion. 4-Chloro-2-(methylthio)pyrimidine reacts similarly to give 2,4-bis(methylthio)pyrimidine, indicating that this reaction may be a general one. The lability of the methylthio group in ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate is also shown by the reaction with an excess of MeONa to give methyl 2,4-dimethoxy-pyrimidine-5-carboxylate. A number of other nucleophilic substitution products derived from ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate are described. 33 references. The experimental part of the paper was very detailed, including the reaction process of Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1Application In Synthesis of Ethyl 2,4-diaminopyrimidine-5-carboxylate)

Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1) belongs to anime. Primary amines having a tertiary alkyl group (R3CNH2) are difficult to prepare with most methods but are made industrially by the Ritter reaction. In this method a tertiary alcohol reacts with hydrogen cyanide (HCN) in the presence of a concentrated strong acid; a formamide, RNH―CHO, is formed first, which then undergoes hydrolysis.Application In Synthesis of Ethyl 2,4-diaminopyrimidine-5-carboxylate

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia