3373-53-3

Basic information

• Product Name: 6-Amino-3,7-dihydro-2H-purin-2-one
• Synonyms: 2-HYDROXY-6-AMINOPURINE;6-AMINO-1,3-DIHYDRO-2H-PURIN-2-ONE;ISOGUANINE;6-Amino-3,7-dihydro-2H-purin-2-one;6-AMINO-1,7-DIHYDROPURIN-2-ONE;2-Hydroxyadenine;A280/A260=3.45;2-HYDROXY-6-AMINOPURINE 98%
• CAS NO: 3373-53-3
• Molecular Formula: C₅H₅N₅O
• Molecular Weight: 151.13
• EINECS: 222-157-6
• Product Categories: Purine;Nucleotides and Nucleosides;Purines;Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Nucleic acids;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals
• Mol File: 3373-53-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 300 °C
• Boiling Point: 273.11°C (rough estimate)
• Appearance: Off-white to slightly beige/Powder
• Density: 1.4456 (rough estimate)
• Refractive Index: 1.8000 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Aqueous Base (Slightly)
• PKA: 5.32±0.40(Predicted)
• Water Solubility: SLIGHTLY SOLUBLE
• Stability: Hygroscopic
• CAS DataBase Reference: 6-Amino-3,7-dihydro-2H-purin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Amino-3,7-dihydro-2H-purin-2-one(3373-53-3)
• EPA Substance Registry System: 6-Amino-3,7-dihydro-2H-purin-2-one(3373-53-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• Hazardous Substances Data: 3373-53-3(Hazardous Substances Data)

Usage

Description

6-Amino-3,7-dihydro-2H-purin-2-one, also known as a nucleotide base, is an oxopurine derivative characterized by the substitution of an amino group at the 6th position of the 3,7-dihydro-purin-2-one structure. It is a white to light yellow crystal powder with significant applications in various industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
6-Amino-3,7-dihydro-2H-purin-2-one is used as an immunostimulator agent for enhancing the immune response in the body. Its role in stimulating the immune system makes it a valuable compound in the development of drugs targeting immune-related conditions and diseases.
Used in Chemical Research:
As a nucleotide base, 6-Amino-3,7-dihydro-2H-purin-2-one serves as an essential building block in the synthesis of various nucleotides and nucleic acids, which are crucial for genetic information storage and transmission in living organisms. Its use in chemical research contributes to the advancement of knowledge in molecular biology and the development of new therapeutic strategies.
Used in Diagnostic Applications:
6-Amino-3,7-dihydro-2H-purin-2-one's interaction with biological systems makes it a potential candidate for use in diagnostic applications, where it can be employed to detect or monitor specific biological processes or conditions related to immune function.

Synthesis Reference(s)

Journal of the American Chemical Society, 81, p. 2442, 1959 DOI: 10.1021/ja01519a042

InChI:InChI=1/C5H5N5O/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1-2H,(H3,6,7,8,9,10,11)

Synthetic route

2-(methylthio)-7H-purin-6-amine (1198-83-0) → isoguanine (3373-53-3)

Conditions	Yield
With ethanol; dihydrogen peroxide
Multi-step reaction with 2 steps 1: chlorine; H2O 2: aq. NaOH solution View Scheme

4,5,6-triamino-1H-pyrimidin-2-one (22715-34-0) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → isoguanine (3373-53-3)

Conditions	Yield
With formic acid at 160℃;

2-methanesulfonyl-7(9)H-purin-6-ylamine (7357-53-1) → isoguanine (3373-53-3)

Conditions	Yield
With sodium hydroxide

6-Amino-2-chlorpurin (1839-18-5) → isoguanine (3373-53-3)

Conditions	Yield
With hydrogenchloride

5-amino-1(3)H-imidazole-4-carboxamidine dihydrochloride → isoguanine (3373-53-3)

Conditions	Yield
With urea at 180℃;
With sodium hydroxide

8-chloro-2-ethoxy-6-amino-purine → isoguanine (3373-53-3)

Conditions	Yield
With phosphonium iodide; hydrogen iodide at 30 - 40℃;

crotonoside → isoguanine (3373-53-3)

Conditions	Yield
With sulfuric acid Hydrogenation;

2,8-dichloro-7(9)H-purin-6-ylamine (2914-09-2) → isoguanine (3373-53-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium/BaSO4; aq. NaOH solution 2: aqueous HCl View Scheme

isoguanine (3373-53-3) → xanthin (69-89-6)

Conditions	Yield
With genes from Klebsiella pneumoniae subsp. pneumoniae In aq. buffer at 30℃; pH=7.5; Kinetics; Temperature; Reagent/catalyst; Enzymatic reaction;

isoguanine (3373-53-3) → 6-amino-2-oxo-1H,7H-purin-3-ium chloride

Conditions	Yield
With hydrogenchloride In water

isoguanine (3373-53-3) → 1,N6-etheno-N9β-D-ribofuranosylisoguanosine + 1,N6-etheno-N7β-D-ribofuranosylisoguanosine + 1,N6-etheno-N6β-D-ribofuranosylisoguanosine

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride; sodium hydrogencarbonate / water / pH Ca. 2 2: ammonium hydroxide; calf spleen purine-nucleoside phosphorylase wild type / aq. buffer / 72 h / 30 °C / pH 7 / Enzymatic reaction View Scheme

isoguanine (3373-53-3) → 1,N6-etheno-N6β-D-ribofuranosylisoguanosine

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride; sodium hydrogencarbonate / water / pH Ca. 2 2: ammonium hydroxide; calf spleen purine-nucleoside phosphorylase-N243D / aq. buffer / 72 h / 30 °C / pH 7 / Enzymatic reaction View Scheme

2-chloroethanal (107-20-0) + isoguanine (3373-53-3) → 1,5,9-dihydro-9-oximidazo[1,2-a]purine

Conditions	Yield
With hydrogenchloride; sodium hydrogencarbonate In water pH=Ca. 2;

Upstream product

• 1198-83-0 2-(methylthio)-7H-purin-6-amine 
• 22715-34-0 4,5,6-triamino-1H-pyrimidin-2-one 
• 77287-34-4 formamide 
• 7357-53-1 2-methanesulfonyl-7⁽⁹⁾H-purin-6-ylamine 
• 1839-18-5 6-Amino-2-chlorpurin 
• 2914-09-2 2,8-dichloro-7⁽⁹⁾H-purin-6-ylamine 
• 66224-66-6 adenine 
• 1904-98-9 2,6-diaminopurine 
• 106449-56-3 2'-deoxyisoguanosine 
• 1818-71-9 1,2-dihydro-2-oxoadenosine 
• 225640-39-1 3-methoxyadenine 
• 10333-86-5 5-(N¹-benzoylthiocarbamoyl)aminoimidazole-4-carboxamide 

Downstream Products

• 1212821-92-5 6-amino-9-trityl-1H-purin-2(9H)-one 
• 69-89-6 xanthin 
• 1818-71-9 isoguanosine 
• 120-89-8 parabanic acid 
• 61066-33-9 pyrimidine-2,4,5,6(1H,3H)-tetraone 
• 57-13-6 urea 

Relevant articles and documents

Regulation of xanthine oxidase activity by substrates at active sites via cooperative interactions between catalytic subunits: Implication to drug pharmacokinetics

Three xanthine oxidase substrates (i.e., xanthine, adenine, and 2-amino-4-hydroxypterin) show a "substrate inhibition" pattern (i.e., slower turnover rates at higher substrate concentrations), whereas another two substrates (i.e., xanthopterin and lumazine) show a "substrate activation" pattern (i.e., higher turnover rates at higher substrate concentrations). Binding of a 6-formylpterin at one of the two xanthine oxidase active sites slows down the turnover rate of xanthine at the adjacent active site from 17.0 s-1 to 10.5 s-1, and converts the V-[S] plot from "substrate inhibition" pattern to a classical Michaelis-Menten hyperbolic saturation pattern. In contrast, binding of xanthine at an active site accelerates the turnover rate of 6-formylpterin at the neighboring active site. The experimental results demonstrate that a substrate can regulate the activity of xanthine oxidase via binding at the active sites; or a xanthine oxidase catalytic subunit can simultaneously serve as a regulatory unit. Theoretical simulation based on the velocity equation derived from the extended Michaelis-Menten model shows that the substrate inhibition and the substrate activation behavior in the V-[S] plots could be obtained by introducing cooperative interactions between two catalytic subunits in homodimeric enzymes. The current work confirms that there exist very strong cooperative interactions between the two catalytic subunits of xanthine oxidase.

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One-Step Synthesis of 2-Fluoroadenine Using Hydrogen Fluoride Pyridine in a Continuous Flow Operation

We report the development of a one-pot synthesis of 2-fluoroadenine from an inexpensive 2,6-diaminopurine starting material using diazonium chemistry in a continuous fashion. Given the sensitivity of this transformation to temperature, we conducted critical experiments to study the exothermicity of the reaction and the heat removal, which were critical for the development of the process. Our goal was to improve the yield and purity of this pharmaceutical intermediate (2-fluoroadenine) and develop a more robust process.

Purines. LXXIX. Synthesis and hydrolysis of 3-methoxyadenine and its N6-benzyl derivative leading to the corresponding 2-hydroxyadenines

Methylation of adenine 3-oxide (8a) with MeI in AcNMe2 afforded 3- methoxyadenine (9a) in 44% yield. This compound (9a) underwent hydroxide-ion attack at the 2-position to give 2-hydroxyadenine (isoguanine) (10a) in 38% yield. A parallel reaction sequence starting from N6-benzyladenine 3-oxide (8c) and proceeding through N6-benzyl-3-methoxyadenine (9c) provided N6- benzyl-2-hydroxyadenine (10c) in 29% overall yield, together with a small amount of N6-benzyladenine (11c).