Category: pyrimidines

Krchnak, V.’s team published research in Collection of Czechoslovak Chemical Communications in 40 | CAS: 56621-93-3

Collection of Czechoslovak Chemical Communications published new progress about 56621-93-3. 56621-93-3 belongs to pyrimidines, auxiliary class Pyrimidine,Nitrile,Amine, name is 5-Aminopyrimidine-2-carbonitrile, and the molecular formula is C5H4N4, Synthetic Route of 56621-93-3.

Krchnak, V. published the artcilePreparation and some reactions of 2,5-substituted pyrimidines, Synthetic Route of 56621-93-3, the publication is Collection of Czechoslovak Chemical Communications (1975), 40(5), 1384-9, database is CAplus.

The title compounds I (X = H, NH2, SH, SMe) were prepared by direct synthesis from [Me2NCH:C(CH:NMe2)N:CHNMe2]+ClO4- and HN:CXNH2. The reactants were reluxed in EtOH with dropwise addition of MeONa and HNEt2 distilled off in vacuo. I (X = H) was accompanied by [Me2NCH:NCH:NMe2]+ClO4- as by-product formed by reaction of liberated HNMe2 with HN:CHNH2. I (X = SMe) gave with NaClO, according to the reaction temperature, I (X = SOMe) or I (X = SO2Me) (II). II was especially ready for nucleophilic substitution of the SO2Me group and gave with alc. MeONa and with KCN in hot DMF, resp., I (X = OMe) and I (X = CN). Reaction of I (X = SH) with Me2SO in the presence of H2SO4 yielded III instead of the expected 2-hydroxypyrimidine derivative The readiness of II to undergo nucleophilic substitution by OMe and CN in the position 2 was compared with 3 addnl. 2-methylsulfonylpyrimidine 5-substituted with NHCHO, NH2, and H. The reaction rate was lowered by electron donating 5-substituents but the order of reactivities was different for OMe and CN.

Collection of Czechoslovak Chemical Communications published new progress about 56621-93-3. 56621-93-3 belongs to pyrimidines, auxiliary class Pyrimidine,Nitrile,Amine, name is 5-Aminopyrimidine-2-carbonitrile, and the molecular formula is C5H4N4, Synthetic Route of 56621-93-3.

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

Krchnak, V.’s team published research in Collection of Czechoslovak Chemical Communications in 40 | CAS: 56621-93-3

Collection of Czechoslovak Chemical Communications published new progress about 56621-93-3. 56621-93-3 belongs to pyrimidines, auxiliary class Pyrimidine,Nitrile,Amine, name is 5-Aminopyrimidine-2-carbonitrile, and the molecular formula is C5H4N4, Name: 5-Aminopyrimidine-2-carbonitrile.

Krchnak, V. published the artcileNovel pyrimidine derivatives, reactions, and ultraviolet spectra, Name: 5-Aminopyrimidine-2-carbonitrile, the publication is Collection of Czechoslovak Chemical Communications (1975), 40(5), 1396-402, database is CAplus.

The conditions were studied for selective hydrolysis of I (R1 = NH2, NMe2, OH, OAc, OMe, SH, SMe, H, F, Cl, Br, SOME2, SO2Me, CN) and the products characterized by uv spectra. Hydrolysis of I in boiling 0.02M H2SO4 or 0.2M AcOH gave the corresponding II, while treating I with 0.2M H2SO4 at 110° or with boiling 5% K2CO3 solution yielded the appropriate III. In strongly alk. media I (R1 = CN) gave III (R1 = CONH2) and III (R1 = CO2H). Special conditions were required for the hydrolysis of I (R1 = F) (IV) which gave in 3M KHF2 at 75° II (R1 = F) and at 120° afforded III (R1 = F), while heating IV in 5% K2CO3 solution yielded III (R1 = NMe2).

Collection of Czechoslovak Chemical Communications published new progress about 56621-93-3. 56621-93-3 belongs to pyrimidines, auxiliary class Pyrimidine,Nitrile,Amine, name is 5-Aminopyrimidine-2-carbonitrile, and the molecular formula is C5H4N4, Name: 5-Aminopyrimidine-2-carbonitrile.

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

Della Sala, Giorgio’s team published research in Journal of Organometallic Chemistry in 692 | CAS: 608-34-4

Journal of Organometallic Chemistry published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione.

Della Sala, Giorgio published the artcileSynthesis of uracil derivatives by oxidation of Fischer tungsten-carbene uracil complexes, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Journal of Organometallic Chemistry (2007), 692(8), 1623-1627, database is CAplus.

A study on the oxidation of Fischer tungsten-carbene uracil complexes has been carried out. E.g., oxidation of Fischer tungsten-carbene uracil complex I by Me3NO gave 78% uracil II. Several commonly used oxidants gave results strongly influenced by the presence of substituents on the nitrogen atoms. In particular, the usual oxidants failed in the oxidation of 3-alkyl uracil carbene complexes. Finally, the authors showed that t-Bu hydroperoxide is able to oxidize successfully 3-alkyl uracil carbene complexes and can be used as a good alternative to the other methods.

Journal of Organometallic Chemistry published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione.

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

Saleh, Amer F.’s team published research in Bioconjugate Chemistry in 21 | CAS: 169396-92-3

Bioconjugate Chemistry published new progress about 169396-92-3. 169396-92-3 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide,Others,PNA, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C26H26N4O7, Safety of 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid.

Saleh, Amer F. published the artcileSynthesis and Splice-Redirecting Activity of Branched, Arginine-Rich Peptide Dendrimer Conjugates of Peptide Nucleic Acid Oligonucleotides, Safety of 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, the publication is Bioconjugate Chemistry (2010), 21(10), 1902-1911, database is CAplus and MEDLINE.

Arginine-rich cell-penetrating peptides have found excellent utility in cell and in vivo models for enhancement of delivery of attached charge-neutral PNA or PMO oligonucleotides. The authors report the synthesis of dendrimeric peptides containing 2- or 4-branched arms each having one or more R-Ahx-R (R = Arg; Ahx = aminohexanoic acid) motifs and their disulfide conjugation to a PNA705 splice-redirecting oligonucleotide. Conjugates were assayed in a HeLa pLuc705 cell assay for luciferase up-regulation and splicing redirection. Whereas 8-Arg branched peptide-PNA conjugates showed poor activity compared to a linear (R-Ahx-R)4-PNA conjugate, 2-branched and some 4-branched 12 and 16 Arg peptide-PNA conjugates showed activity similar to that of the corresponding linear peptide-PNA conjugates. Many of the 12- and 16-Arg conjugates retained significant activity in the presence of serum. Evidence showed that biol. activity in HeLa pLuc705 cells of the PNA conjugates of branched and linear (R-Ahx-R) peptides is associated with an energy-dependent uptake pathway, predominantly clathrin-dependent, but also with some caveolae dependence.

Bioconjugate Chemistry published new progress about 169396-92-3. 169396-92-3 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide,Others,PNA, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C26H26N4O7, Safety of 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid.

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

Saleh, Amer F.’s team published research in Bioconjugate Chemistry in 21 | CAS: 186046-81-1

Bioconjugate Chemistry published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, Computed Properties of 186046-81-1.

Saleh, Amer F. published the artcileSynthesis and Splice-Redirecting Activity of Branched, Arginine-Rich Peptide Dendrimer Conjugates of Peptide Nucleic Acid Oligonucleotides, Computed Properties of 186046-81-1, the publication is Bioconjugate Chemistry (2010), 21(10), 1902-1911, database is CAplus and MEDLINE.

Arginine-rich cell-penetrating peptides have found excellent utility in cell and in vivo models for enhancement of delivery of attached charge-neutral PNA or PMO oligonucleotides. The authors report the synthesis of dendrimeric peptides containing 2- or 4-branched arms each having one or more R-Ahx-R (R = Arg; Ahx = aminohexanoic acid) motifs and their disulfide conjugation to a PNA705 splice-redirecting oligonucleotide. Conjugates were assayed in a HeLa pLuc705 cell assay for luciferase up-regulation and splicing redirection. Whereas 8-Arg branched peptide-PNA conjugates showed poor activity compared to a linear (R-Ahx-R)4-PNA conjugate, 2-branched and some 4-branched 12 and 16 Arg peptide-PNA conjugates showed activity similar to that of the corresponding linear peptide-PNA conjugates. Many of the 12- and 16-Arg conjugates retained significant activity in the presence of serum. Evidence showed that biol. activity in HeLa pLuc705 cells of the PNA conjugates of branched and linear (R-Ahx-R) peptides is associated with an energy-dependent uptake pathway, predominantly clathrin-dependent, but also with some caveolae dependence.

Bioconjugate Chemistry published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, Computed Properties of 186046-81-1.

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

Stoner, Eric J.’s team published research in Organic Process Research & Development in 2000-08-31 | CAS: 192725-50-1

Organic Process Research & Development published new progress about ABT378 lopinavir large scale synthesis; oxopyrimidineacetate large scale synthesis. 192725-50-1 belongs to class pyrimidines, name is (S)-3-Methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanoic acid, and the molecular formula is C9H16N2O3, HPLC of Formula: 192725-50-1.

Stoner, Eric J. published the artcileSynthesis of HIV Protease Inhibitor ABT-378 (Lopinavir), HPLC of Formula: 192725-50-1, the main research area is ABT378 lopinavir large scale synthesis; oxopyrimidineacetate large scale synthesis.

A large-scale process for the synthesis of HIV protease inhibitor candidate ABT-378 was developed which utilizes an intermediate common to the synthesis of ritonavir, Abbott’s first generation compound The synthesis relies on the sequential acylation of this intermediate which is carried through as a mixture of diastereomers until the penultimate step. A synthesis of (S)-tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetate, derived from L-valine, is also reported.

Organic Process Research & Development published new progress about ABT378 lopinavir large scale synthesis; oxopyrimidineacetate large scale synthesis. 192725-50-1 belongs to class pyrimidines, name is (S)-3-Methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanoic acid, and the molecular formula is C9H16N2O3, HPLC of Formula: 192725-50-1.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Sakamoto, Takao’s team published research in Heterocycles in 1978-04-01 | CAS: 67073-96-5

Heterocycles published new progress about homolytic regioselective acylation pyrimidine. 67073-96-5 belongs to class pyrimidines, name is 1-(6-Methylpyrimidin-4-yl)ethanone, and the molecular formula is C7H8N2O, Safety of 1-(6-Methylpyrimidin-4-yl)ethanone.

Sakamoto, Takao published the artcileSelectivity on the homolytic acylation of pyrimidine derivatives, Safety of 1-(6-Methylpyrimidin-4-yl)ethanone, the main research area is homolytic regioselective acylation pyrimidine.

Pyrimidines I [R, R1 = H, Ph; H, Me; RR1 = (CH2)4] were treated with acetyl radical, generated from R2CHO (R2 = Me) FeSO4, tert-BuOOH and H2SO4, to give 25-45% the 4-acetyl derivatives II (R2 = Ac). No 2-acetyl derivatives were formed. Similar reactions using I (R = H, R1 = Ph) and R2CHO (R2 = Et, iso-Pr, Ph) gave 28-50% corresponding II.

Heterocycles published new progress about homolytic regioselective acylation pyrimidine. 67073-96-5 belongs to class pyrimidines, name is 1-(6-Methylpyrimidin-4-yl)ethanone, and the molecular formula is C7H8N2O, Safety of 1-(6-Methylpyrimidin-4-yl)ethanone.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Newmark, Philip’s team published research in Biochimica et Biophysica Acta in 1962 | CAS: 19030-75-2

Biochimica et Biophysica Acta published new progress about LIVER/metabolism; NUCLEASES/metabolism; PHOSPHORYLASES/metabolism. 19030-75-2 belongs to class pyrimidines, name is 5-N-Propyluracil, and the molecular formula is C7H10N2O2, Recommanded Product: 5-N-Propyluracil.

Newmark, Philip published the artcileSubstrate specificity of the dihydrouracil dehydrogenase and uridine phosphorylase of rat liver, Recommanded Product: 5-N-Propyluracil, the main research area is LIVER/metabolism; NUCLEASES/metabolism; PHOSPHORYLASES/metabolism.

Studies were conducted to determine whether unnatural pyrimidines (e.g. 5-fluorouracil) which are able to inhibit the degradation of uracil and thymine in a complete rat-liver-enzyme system were the only ones reduced by dihydrouracil dehydrogenase (I), and whether reduction of the inhibiting pyrimidines by the I was a prerequisite for inhibition. Thymine reduction was slower than that of uracil. The relative rates of reduction of 5-halagenouracils were F > Cl > Br > I, 5-iodouracil being slower than uracil and 5-fluoro-uracil faster. I reduced 2-thiouracil, 6-azamacil, and 5-aminouracil relatively slowly. 5-Hydroxyuracil and 5alkyluracils were not reduced, but were effective inhibitors of uracil and thymine degradation. Neither cytosine nor 6-methyluracil acted in either capacity.

Biochimica et Biophysica Acta published new progress about LIVER/metabolism; NUCLEASES/metabolism; PHOSPHORYLASES/metabolism. 19030-75-2 belongs to class pyrimidines, name is 5-N-Propyluracil, and the molecular formula is C7H10N2O2, Recommanded Product: 5-N-Propyluracil.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Pluskota, Donata’s team published research in Synthetic Communications in 1992-11-30 | CAS: 19030-75-2

Synthetic Communications published new progress about methylcytosine; cytosine alkyldimethyl. 19030-75-2 belongs to class pyrimidines, name is 5-N-Propyluracil, and the molecular formula is C7H10N2O2, Related Products of pyrimidines.

Pluskota, Donata published the artcileThe facile synthesis of N(1), N(4)-dimethyl-5-substituted cytosines, Related Products of pyrimidines, the main research area is methylcytosine; cytosine alkyldimethyl.

A facile, high yield synthesis of N(1),N(4)-dimethyl-5-alkylcytosines is described. Thus chlorination of alkyluracils I (R = Me, Et, Pr, Bu) followed by substitution with NaOEt and methylation gave methylpyrimidinones II (R1 = EtO). Substitution of II (R1 = EtO) with MeNH2 gave the title compounds II (R1 = MeNH). This method is an alternative and universal route to N(1),N(4)-methylated cytosines with any 5-substituent.

Synthetic Communications published new progress about methylcytosine; cytosine alkyldimethyl. 19030-75-2 belongs to class pyrimidines, name is 5-N-Propyluracil, and the molecular formula is C7H10N2O2, Related Products of pyrimidines.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Felczak, Krzysztof’s team published research in Collection Symposium Series in 1999 | CAS: 19030-75-2

Collection Symposium Series published new progress about phenylseleno uracil preparation virucide HIV. 19030-75-2 belongs to class pyrimidines, name is 5-N-Propyluracil, and the molecular formula is C7H10N2O2, Synthetic Route of 19030-75-2.

Felczak, Krzysztof published the artcileSynthesis of novel acyclo 6-(phenylseleno)uracils – potential selective anti-HIV agents, Synthetic Route of 19030-75-2, the main research area is phenylseleno uracil preparation virucide HIV.

Starting from 5-propyluracil regioselective syntheses of 1-[(2-hydroxyethoxy)methyl]-6-(phenylseleno)-5-propyluracil, 1-(ethoxymethyl)-6-(phenylseleno)-5-propyluracil and 1-(benzyloxymethyl)-6-(phenylseleno)-5-propyluracil were described. The biol. and pharmacol. activity of the compounds thus prepared was not reported.

Collection Symposium Series published new progress about phenylseleno uracil preparation virucide HIV. 19030-75-2 belongs to class pyrimidines, name is 5-N-Propyluracil, and the molecular formula is C7H10N2O2, Synthetic Route of 19030-75-2.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia