54326-16-8

Usage

Uses

Used in Pharmaceutical Industry:
5-CHLORO-2-HYDROXYPYRIMIDINE is used as a chemical intermediate for the preparation of dimethoxy-pyrrolidylquinazolines, which are brain penetrable PDE10A inhibitors. These inhibitors have potential applications in the treatment of various neurological and psychiatric disorders, such as schizophrenia and Huntington's disease, due to their ability to modulate the activity of phosphodiesterase 10A (PDE10A), an enzyme involved in signal transduction pathways in the brain.
Additionally, 5-CHLORO-2-HYDROXYPYRIMIDINE is used in the synthesis of platinum(II) hydroxypyrimidinato ethylenediamine tetranuclear metallacalix[4]arene complexes. These complexes have potential applications in the field of cancer chemotherapy, as they may exhibit unique properties and activities that could be beneficial in the treatment of various types of cancer.

InChI:InChI=1/C4H3ClN2O/c5-3-1-6-4(8)7-2-3/h1-2H,(H,6,7,8)

Upstream product

• 557-01-7 2-hydroxypyrimidine 
• 36437-19-1 2-chloromalonaldehyde 
• 57-13-6 urea 
• 119451-81-9 1-(tert-butyldimethylsilyloxy)methyl-5-chloro-2(1H)-pyrimidinone 

Downstream Products

• 22536-67-0 2,5-dichloropyrimidine 
• 103594-88-3 2-(benzyloxy)methoxy-5-chloropyrimidine 
• 88045-77-6 1-(benzyloxy)methyl-5-chloro-2(1H)-pyrimidinone 
• 144708-15-6 5-chloro-2-phenylsulfenylmethoxypyrimidine 
• 115171-54-5 5-chloro-2-(4-chlorobenzyloxy)methoxypyrimidine 
• 88045-78-7 5-chloro-1-(4-chlorobenzyloxy)methyl-2(1H)-pyrimidinone 
• 83768-20-1 5-chloro-1-(4-methoxyphenylsulfenyl)methyl-2(1H)-pyrimidinone 
• 83768-19-8 5-chloro-2-(4-methoxyphenylsulfenyl)methyloxypyrimidine 
• 83767-97-9 5-chloro-2-(phenoxy)-methoxypyrimidine 
• 83767-98-0 5-chloro-1-(phenoxy)methyl-2(1H)-pyrimidinone 
• 83767-93-5 5-chloro-2-(4-chlorophenylsulfenyl)methyloxypyrimidine 
• 83767-86-6 5-chloro-1-(4-chlophenylsulfenyl)methyl-2(1H)-pyrimidinone 
• 88045-94-7 1-(α-benzylthiobenzyl)-5-chloro-2(1H)-pyrimidinone 
• 115171-56-7 Benzyl-(5-chloro-pyrimidin-2-yloxymethyl)-carbamic acid ethyl ester 

Relevant academic research and scientific papers

An improved synthesis of [2-14C]2, 5-dichloropyrimidine

A previously described, five-step synthesis of [2-14C]2, 5-dichloropyrimidine was based on condensation of [14C]urea with an acetal, followed by bromination, chlorination, boronic acid formation, and finally chlorination. This improved synthesis also started from readily available [14C]urea, which was condensed with 2-chloromalonaldehyde, followed by chlorination with POCl3 yielding [2-14C]2, 5-dichloropyrimidine with a radiochemical purity of 99% in an overall radiochemical yield of 72%. Copyright

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.

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.

(tert-Butyldimethylsilyloxy)methyl Chloride: Synthesis and Use as N-protecting Group in Pyrimidinones

A new reagent, (tert-butyldimethylsilyloxy)methyl chloride (3) has been synthesized by sulfuryl chloride cleavage of (tert-butyldimethylsilyloxy)methyl ethyl sulfide (2).The latter was prepared from tert-butyldimethylsilyl chloride and ethylthiomethanol.The chloromethyl ether 3 has been used for the protection of the NH functionality in 5-halo-2(1H)-pyrimidinones and for the protection of the N-1 in N-3 alkylation of thymine.