557-01-7

Usage

Purification Methods

It crystallises from EtOH or ethyl acetate. Its solubility in H2O at 20o is 1g/2.2mL. [Albert J Chem Soc 4219 1952, Beilstein 24 III/IV 194.]. 2-Hydroxypyrimidine hydrochloride [38353-09-2] M 132.5, has m 203-205.5o(dec)

InChI:InChI=1/C4H4N2O/c7-4-5-2-1-3-6-4/h1-3H,(H,5,6,7)

Upstream product

• 109-12-6 2-aminopyrimidine 
• 823-09-6 2-(methylsulfanyl)pyrimidine 
• 80927-55-5 4-chloro-1H-pyrimidin-2-one 
• 122-31-6 malondialdehyde bis(diethyl acetal) 
• 57-13-6 urea 
• 557-01-7 2-hydroxypyrimidine 
• 31575-35-6 2-fluoropyrimidine 
• 3739-82-0 2-ethoxy-pyrimidine 
• 3739-83-1 2-isopropoxypyrimidine 
• 110-89-4 piperidine 
• 77287-34-4 formamide 
• 3690-10-6 Zebularine 
• 42563-68-8 2,4,6,8-tetraazabicyclo[3.3.1]nonane-3,7-dione 
• 102-52-3 malonaldehydebis(dimethylacetal) 

Downstream Products

• 3739-81-9 1-methyl-1H-pyrimidin-2-one 
• 931-63-5 2-methoxypyrimidine 
• 52523-22-5 2-trimethylsilyloxypyrimidine 
• 99272-07-8 [2,2-Dimethyl-5-(pyrimidin-2-yloxymethyl)-[1,3]dioxolan-4-yl]-methanol 
• 99272-05-6 Benzoic acid 2,2-dimethyl-5-(2-oxo-2H-pyrimidin-1-ylmethyl)-[1,3]dioxolan-4-ylmethyl ester 
• 99272-15-8 4-(p-Toluenesulfonyloxymethyl)-5-(2-pyrimidon-1-yl)methyl-2,2-dimethyl-(4S,5S)-1,3-dioxolane 
• 95209-83-9 2-(2-oxopyrimidin-1(2H)-yl)acetic acid 
• 38353-06-9 5-bromo-1H-pyrimidin-2-one 
• 66-22-8 uracil 
• 79387-69-2 5-iodo-2(1H)-pyrimidinone 
• 557-01-7 2-hydroxypyrimidine 
• 68753-37-7 1-<2'-deoxy-3',5'-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl>-2(1H)-pyrimidinone 
• 121012-93-9 2-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyloxy>pyrimidine 
• 5585-14-8 3,4-diphenyl-furazan 2-oxide 

Relevant academic research and scientific papers

Template-directed synthesis of cucurbituril analogues using propanediurea as a building block

Two novel cucurbituril-like macrocycles, TD[4] and TD[5], were prepared from the condensation of propanediurea and formaldehyde using CaCl2 and BaCl2 as templates, respectively, featuring convenience and low cost. The two hosts show excellent thermostability and their structures were characterized by 1H NMR, HRMS and single crystal X-ray diffraction.

Discovery of BI 207524, an indole diamide NS5B thumb pocket 1 inhibitor with improved potency for the potential treatment of chronic hepatitis C virus infection

The development of interferon-free regimens for the treatment of chronic HCV infection constitutes a preferred option that is expected in the future to provide patients with improved efficacy, better tolerability, and reduced risk for emergence of drug-resistant virus. We have pursued non-nucleoside NS5B polymerase allosteric inhibitors as combination partners with other direct acting antivirals (DAAs) having a complementary mechanism of action. Herein, we describe the discovery of a potent follow-up compound (BI 207524, 27) to the first thumb pocket 1 NS5B inhibitor to demonstrate antiviral activity in genotype 1 HCV infected patients, BILB 1941 (1). Cell-based replicon potency was significantly improved through electronic modulation of the pKa of the carboxylic acid function of the lead molecule. Subsequent ADME-PK optimization lead to 27, a predicted low clearance compound in man. The preclinical profile of inhibitor 27 is discussed, as well as the identification of a genotoxic metabolite that led to the discontinuation of the development of this compound.

Meteorites as catalysts for prebiotic chemistry

From outer space: Twelve meteorite specimens, representative of their major classes, catalyse the synthesis of nucleobases, carboxylic acids, aminoacids and low-molecular-weight compounds from formamide (see figure). Different chemical pathways are identified, the yields are high for a prebiotic process and the products come in rich and composite panels.

Synthesis, characterization and pharmacological study of 4,5-dihydropyrazolines carrying pyrimidine moiety

A series of 5-bromo-2-(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)pyrimidine were prepared under conventional heating as well as microwave reaction condition. The newly synthesized compounds were characterized on the basis of elemental, spectral and single crystal X-ray studies. These new compounds were screened for their antioxidant, anti-inflammatory and analgesic activities. Some of these compounds exhibited potent biological activities compared to the standard drug.

Comprehensive investigation of the energetics of pyrimidine nucleoside formation in a model prebiotic reaction

The problem of β-nucleoside formation under prebiotic conditions represents one of the most significant challenges to the "RNA world" hypothesis. The possibility exists that alternative bases may have come before the contemporary bases (i.e., A, G, C, and

Synthesis and degradation of nucleic acid components by formamide and iron sulfur minerals

We describe the one-pot synthesis of a large panel of nucleic bases and related compounds from formamide in the presence of iron sulfur and iron-copper sulfur minerals as catalysts. The major products observed are purine, 1H-pyrimidinone, isocytosine, adenine, 2-aminopurine, carbodiimide, urea, and oxalic acid. Isocytosine and 2-aminopurine may recognize natural nucleobases by Watson-Crick and reverse Watson-Crick interactions, thus suggesting novel scenarios for the origin of primordial nucleic acids. Since the major problem in the origin of informational polymers is the instability of their precursors, we also investigate the effects of iron sulfur and iron-copper sulfur minerals on the stability of ribooligonucleotides in formamide and in water. All of the iron sulfur and iron-copper sulfur minerals stimulated degradation of RNA. The relevance of these findings with respect to the origin of informational polymers is discussed.

VIRAL POLYMERASE INHIBITORS

The present invention relates to compounds represented by formula (I) wherein A, B, D, E, R2, R3, R4, R5, R6, R9, a, b, d and e are as defined herein, their salt or ester and pharmaceutical compositions thereof useful in the treatment of hepatitis C viral (HCV) infection. Said compounds were found to have inhibitory activity against HCV polymerase, especially as inhibitors of HCV NS5B polymerase

VIRAL POLYMERASE INHIBITORS

A compound, represented by formula (I) or an enantiomer, diastereoisomer or tautomer thereof : wherein either A or B is nitrogen and the other B or A is C, and the radicals R1, R2, R3, R5, R6, R7, R9, and R10 are as defined herein, or a salt, ester or derivative thereof as viral polymerase inhibitors. The compound is used as an inhibitor of RNA dependent RNA polymerases, particulary those viral polymerases within the Flaviviridae family, more particulary to HCV polymerase.

Hydrogen peroxide promoted hydroxylation of haloarenes and heteroarenes

Addition of aqueous hydrogen peroxide significantly accelerates the substitution reactions of hydroxide salts with haloarenes bearing electron withdrawing substituents. A similar effect is observed in the reactions of hydroxide salts with halogenated heteroarenes. Reactions are carried out in water or water-THF at ambient temperature or at 50-60 °C.

COMPOUNDS USEFUL AS ANTIPROLIFERATIVE AGENTS AND GARFT INHIBITORS

The invention relates to compounds, such as compound (1) in equilibrium with its 4-hydroxy tautomer, and its pharmaceutically acceptable salts. Such compounds are useful as inhibitors of glycinamide ribonucleotide formyl transferase (GARFT) or as antiproliferative agents. The invention also pertains to pharmaceutical compositions and methods employing such compounds as GARFT inhibitors or antiproliferative agents. The invention also relates to compounds useful as intermediates for preparing such compounds.