1194-21-4

Basic information

• Product Name: 2-Amino-6-chloro-4-pyrimidinol
• Synonyms: AKOS 92811;2-AMINO-4-HYDROXY-6-CHLOROPYRIMIDINE;2-AMINO-6-CHLORO-4-HYDROXYPYRIMIDINE;2-AMINO-4-CHLORO-6-HYDROXYPYRIMIDINE;2-AMINO-4-CHLORO-6-PYRIMIDINOL;TIMTEC-BB SBB004114;2-amino-6-chloro-4(1h)-pyrimidinon;2-amino-6-chloro-4-pyrimidino
• CAS NO: 1194-21-4
• Molecular Formula: C₄H₄ClN₃O
• Molecular Weight: 145.55
• EINECS: 214-785-4
• Product Categories: PYRIMIDINE
• Mol File: 1194-21-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 252 °C (dec.)(lit.)
• Boiling Point: 259.1 °C at 760 mmHg
• Flash Point: 110.5 °C
• Appearance: /
• Density: 1.7910 (rough estimate)
• Vapor Pressure: 0.00676mmHg at 25°C
• Refractive Index: 1.4510 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Sparingly)
• PKA: 7.49±0.50(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2-Amino-6-chloro-4-pyrimidinol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-6-chloro-4-pyrimidinol(1194-21-4)
• EPA Substance Registry System: 2-Amino-6-chloro-4-pyrimidinol(1194-21-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22-20/21/22
• Safety Statements: 26-36-36/37-24/25
• WGK Germany: 3
• RTECS: UW5995000
• Hazardous Substances Data: 1194-21-4(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

2-?Amino-?6-?chloro-?4-?pyrimidinol is used to prepare O- and N-phosphonomethoxyalkyl pyrimidines with antiviral activities. It is also used to synthesize (±)?-?9-?[[(Z)?-?2-?(hydroxymethyl)?cyclopropyl]?methyl]?guanine with antiherpetic activities.

InChI:InChI=1/C4H4ClN3O/c5-2-1-3(9)8-4(6)7-2/h1H2,(H2,6,8,9)

Upstream product

• 56-05-3 2-Amino-4,6-dichloropyrimidine 
• 5734-64-5 2-amino-4-chloro-6-methoxypyrimidine 
• 56-09-7 2-amino-6-hydroxy-pyrimidin-4(3H)-one 
• 1193-21-1 4,6-dichloropyrimidine 
• 37517-81-0 3-chloro-3-oxopropanoic acid methyl ester 
• 50-01-1 guanidine hydrochloride 

Downstream Products

• 164525-11-5 2-amino-6-ethylaminopyrimidin-4(3H)-one 
• 1077-04-9 2-amino-6-(2-hydroxy-ethylamino)-3H-pyrimidin-4-one 
• 54004-20-5 2-amino-6-(methylamino)pyrimidin-4(3H)-one 
• 89033-32-9 2-amino-6-thioxo-5,6-dihydro-1H-pyrimidin-4-one 
• 1131-35-7 7,8-dihydroxanthopterin 
• 90000-49-0 2-amino-6-(n-propylamino)pyrimidin-4(3H)-one 
• 98510-50-0 2-amino-6-(3-phenylpropyl)aminopyrimidin-4(3H)-one 
• 60462-36-4 2-Amino-6-cyclohexylamino-3H-pyrimidin-4-one 
• 57628-56-5 2-Amino-4,6-di(p-toluidino)pyrimidine 
• 164525-12-6 2-amino-6-isopropylaminopyrimidin-4(3H)-one 
• 60462-37-5 2-amino-6-butylamino-3H-pyrimidin-4-one 
• 5457-91-0 2-Amino-4-n-butylamino-6-chloropyrimidine 
• 37409-94-2 2-amino-6-(benzylmethylamino)-4-pyrimidinol 
• 7400-24-0 2-Amino-6-cyclopentylamino-3H-pyrimidin-4-one 

Relevant articles and documents

Microwave-assisted synthesis and docking studies of phenylureas as candidates for the drug design against the biological warfare agent Yersinia pestis

Background: Bubonic plague is amongst the diseases with the highest potential for being used in biological warfare attacks today. Introduction: This disease, caused by the bacterium Yersina pestis, is highly infectious and can achieve 100% of fatal victims when in its most dangerous form. Besides, there is no effective vac-cine, and the chemotherapy available today against plague is ineffective if not administered at the beginning of the infection. Willing to contribute for changing this reality we propose here new phe-nylureas as candidates for the drug design against plague meant to target the enzyme dihydrofolate reductase from Y. pestis (YpDHFR). Methods: Seven phenylureas, four of them new, were synthesized, following synthetic routes adapted from procedures available in the literature, and using microwave irradiation. After, they were submitted to docking studies inside YpDHFR and human DHFR (HssDHFR) in order to check their potential as selective inhibitors. Results & Conclusion: Our results revealed four new phenylureas and a new synthetic route for this kind of molecule using microwave irradiation. Also, our docking studies pointed to two of the phe-nylureas as selective inhibitors of YpDHFR and, therefore, candidates for the design of new drugs against plague.

Hydrogen-bonded deugdan heterocomplex: Structure and stability and a scalable synthesis of DeUG with reactive functionality

A convenient, scalable synthesis of the supramolecular building block 7-deazaguanine-based urea (DeUG) is reported. Incorporation of reactive moieties (DeUG azide 10 and alkyne 11 for copper-catalyzed azide-alkyne cycloadditions, "click chemistry") and a demonstration of transesterification (DeUG glycol, 12) highlights the versatility. X-ray structures of DeUG and a DeUG-DAN heterocomplex were obtained. Kassoc for the 1.2 heterocomplex was estimated to be 2 x 108 M-1 in chloroform.

2-Amino-6-iodo-4-tosyloxypyrimidine: a versatile key intermediate for regioselective functionalization of 2-aminopyrimidines in 4- and 6-positions

2-Amino-6-iodo-4-tosyloxypyrimidine, easily prepared from commercially available material, is a key intermediate for the preparation of differentially substituted 2-aminopyrimidines by means of sequenced Suzuki and/or Sonogashira reactions.