54326-16-8

Basic information

• Product Name: 5-CHLORO-2-HYDROXYPYRIMIDINE
• Synonyms: 5-chloro-2(1h)-pyrimidinon;5-Chloro-2(1H)-pyrimidinone;5-Chloropyrimidin-2-one;NY 3000;ny3000;5-chloro-1H-pyrimidin-2-one;2(1H)-Pyrimidinone, 5-chloro- (9CI);5-Chloropyrimidin-2-ol
• CAS NO: 54326-16-8
• Molecular Formula: C₄H₃ClN₂O
• Molecular Weight: 130.53
• EINECS: 259-106-2
• Product Categories: PYRIMIDINE;Pyridines, Pyrimidines, Purines and Pteredines;Heterocycle-Pyrimidine series
• Mol File: 54326-16-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 237-238 °C (decomp)
• Appearance: /
• Density: 1.55 g/cm^3/sup>
• Refractive Index: 1.632
• Storage Temp.: 2-8°C
• PKA: 7.62±0.10(Predicted)
• CAS DataBase Reference: 5-CHLORO-2-HYDROXYPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-2-HYDROXYPYRIMIDINE(54326-16-8)
• EPA Substance Registry System: 5-CHLORO-2-HYDROXYPYRIMIDINE(54326-16-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 54326-16-8(Hazardous Substances Data)

Usage

Description

5-CHLORO-2-HYDROXYPYRIMIDINE is a pale yellow crystalline compound that serves as a key intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its unique chemical structure, which allows it to be used in the preparation of different molecules with potential applications in the medical field.

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

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

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 articles and documents

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

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

(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.