452-06-2

Basic information

• Product Name: 2-Aminopurine
• Synonyms: 1H-PURINE-2-AMINE;2-AMINOPURINE, HYDROCHLORIDE;2-AMINOPURINE;1H-Purin-2-amine;2-amino-purin;9H-Purin-2-amine;SQ 22,451;SQ 22451
• CAS NO: 452-06-2
• Molecular Formula: C₅H₅N₅
• Molecular Weight: 135.13
• EINECS: 207-197-4
• Product Categories: PYRIMIDINE;Purine;Nucleotides and Nucleosides;Purines;Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Nucleic acids;Bases & Related Reagents;Nucleotides;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides;Biochemicals and Reagents;Heterocycles
• Mol File: 452-06-2.mol
• Article Data: 17

Chemical Properties

• Melting Point: 280-282 °C(lit.)
• Boiling Point: 238.81°C (rough estimate)
• Flash Point: 362.9 °C
• Appearance: Light beige/Amorphous Powder
• Density: 1.3795 (rough estimate)
• Vapor Pressure: 0.00172mmHg at 25°C
• Refractive Index: 1.7000 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Aqueous Acid (Slightly), Methanol (Slightly, Heated)
• PKA: 8.02±0.20(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2-Aminopurine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminopurine(452-06-2)
• EPA Substance Registry System: 2-Aminopurine(452-06-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 22-36-26
• WGK Germany: 3
• RTECS: UO7475000
• Hazardous Substances Data: 452-06-2(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 452-06-2 differently. You can refer to the following data:
1. A probe of structural dynamics and charge transfer in DNA .
2. 2-Aminopurine has been used to inhibit eukaryotic initiation factor-2α (eIF2α)-phosphorylation of osteoarthritis (OA) chondrocytes.
3. A probe of structural dynamicas and charge transfer in DNA

Definition

ChEBI: The parent compound of the 2-aminopurines, comprising a purine core carrying an amino substituent at the 2-position.

Biochem/physiol Actions

2-Aminopurine (2AP) is an analog of guanosine and adenosine, which can base pair with cytosine and thymine. It is used as a fluorescent probe in nucleic acid structure and dynamics. 2-Aminopurine (2-AP) inhibits double-stranded RNA-dependent protein kinase, protein kinase R (PKR).

Safety Profile

Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-3H,(H2,6,8,9,10)

Synthetic route

2-(methylthio)-9H-purine (33512-51-5) → 9H-purin-2-amine (452-06-2)

Conditions	Yield
With potassium amide In ammonia for 70h; Mechanism; 2-halogenated purines;	90%

2-Amino-6-chloropurin (10310-21-1) → 9H-purin-2-amine (452-06-2)

Conditions	Yield
In hydrogenchloride at 50℃; electrolysis, -0.75V, initial current 50-60 mA;	85%
palladium on charcoal In sodium hydroxide; water

1,2-diaminopurinium mesitylenesulphonate → 9H-purin-2-amine (452-06-2)

Conditions	Yield
With methylamine In methanol at 100℃; for 17h;	80%

1,2-diaminopurinium mesitylenesulphonate → purine (120-73-0) + 9H-purin-2-amine (452-06-2)

Conditions	Yield
With ammonia In methanol at 100℃; for 17h; Mechanism; Product distribution;	A 70% B 20%

pyrimidine-2,4,5-triamine (3546-50-7) + dimethoxymethyl acetate (14036-53-4) → 9H-purin-2-amine (452-06-2)

Conditions	Yield
1.) RT, 6 h, 2.) reflux, 30 min;	61%

1-amino-2-(methylthio)purinium mesitylenesulfonate → 2-(methylthio)-9H-purine (33512-51-5) + 9H-purin-2-amine (452-06-2)

Conditions	Yield
With ammonia In methanol at 100℃; for 17h; Product distribution; Mechanism; ANRORC and no ANRORC mechanism determined by reaction with 15N labelled ammonia; var. temp. and time;	A 55% B 25%

amipurimycin (61991-08-0) → 9H-purin-2-amine (452-06-2)

Conditions	Yield
With trifluoroacetic acid at 130℃;	48%

6-(2-acetylvinylthio)-2-aminopurine → 9H-purin-2-amine (452-06-2)

Conditions	Yield
With nickel In water for 7.5h; Heating;	35.7%

iso-2',3'-dideoxyadenosine (107550-74-3) → 2,3-Didesoxy-β-D-glycero-pentofuranose (122999-44-4) + 9H-purin-2-amine (452-06-2)

Conditions	Yield
With hydrogenchloride at 22℃; rate of hydrolysis relative to dideoxyadenosine;

2-amino-9-(β-D-2'-deoxyribofuranosyl)-purine (3616-24-8) → 2,4-diamino-5-formamidopyrimidine (18620-60-5) + 9H-purin-2-amine (452-06-2)

Conditions	Yield
With sodium cacodylate buffer; water at 110℃; for 22h; Kinetics; Thermodynamic data; Mechanism; ΔH(excit.); var. temp. and times;

thioguanine (154-42-7) → 9H-purin-2-amine (452-06-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / NaOH / dioxane; H2O / 5 - 10 °C 2: 35.7 percent / Raney nickel / H2O / 7.5 h / Heating View Scheme

formamide (77287-34-4, 77287-35-5, 60100-09-6) → 9H-purin-2-amine (452-06-2)

Conditions	Yield
With Canyon Diablo iron meteorites at 140℃; for 24h; Reagent/catalyst; Temperature;

9H-purin-2-amine (452-06-2) → 2-aminopurine thallium salt

Conditions	Yield
With thallium (I) ethoxide In ethanol at 15 - 20℃; for 36h;	92%

9H-purin-2-amine (452-06-2) + 2'-deoxy-2'-fluorouridine (56287-17-3, 69123-94-0, 784-71-4) → 2-amino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine

Conditions	Yield
In water at 37℃; for 48h; thymidine phosphorylase, purine nucleoside phosphorylase, phosphate buffer, pH 7;	89%

9H-purin-2-amine (452-06-2) + 2'-Deoxycytidine (951-77-9) → 2-amino-9-(β-D-2'-deoxyribofuranosyl)-purine (3616-24-8)

Conditions	Yield
With citrate buffer; N-deoxyribosyltransferase from L. leichmannii In ethanol at 40℃; for 48h;	86%

tert-butyl 4-bromobutyrate (110661-91-1) + 9H-purin-2-amine (452-06-2) → C13H19N5O2 (1043904-91-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 80℃;	85%

9H-purin-2-amine (452-06-2) + 1,2:5,6-dianhydro-3,4-di-O-benzyl-L-iditol (157363-84-3) → 1-(2-amino-9H-purin-9-yl)-2,5-anhydro-3,4-di-O-benzyl-1-deoxy-D-glucitol

Conditions	Yield
Stage #1: 9H-purin-2-amine With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: 1,2:5,6-dianhydro-3,4-di-O-benzyl-L-iditol In N,N-dimethyl-formamide at 110℃;	66%

sodium phenyl-methanolate (20194-18-7) + 9H-purin-2-amine (452-06-2) → N-(phenylmethyl)-aminopurine

Conditions	Yield
at 130℃; for 17h;	63%

mesitylenesulfonylhydroxylamine (36016-40-7) + 9H-purin-2-amine (452-06-2) → 1,2-diaminopurinium mesitylenesulphonate

Conditions	Yield
In methanol; dichloromethane for 4h; Ambient temperature;	62%

araU (3083-77-0) + 9H-purin-2-amine (452-06-2) → 2-amino-9-(β-D-arabinofuranosyl)purine

Conditions	Yield
With phosphate buffer; cell paste of Enterobacter aerogenes AJ 11125 at 60℃; for 15h; pH 7.0;	61%

4-acetoxy-3-(acetoxymethyl)-1-iodobutane (127047-77-2) + 9H-purin-2-amine (452-06-2) → 7-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine (131266-15-4) + 9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine (104227-87-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 18h; Ambient temperature;	A 15% B 59%

tert-butyl prop-2-ynoate (13831-03-3) + 9H-purin-2-amine (452-06-2) → C12H15N5O2 (1043904-89-7) + C12H15N5O2 (1043904-90-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 80℃;	A 57% B 23%

9H-purin-2-amine (452-06-2) + cis/trans-1-acetoxymethyl-2-bromo-2-(bromomethyl)cyclopropane → (Z,E)-2-amino-7-[(2-acetoxymethyl)cyclopropylidenemethyl]purine + (Z,E)-2-amino-9-[(2-acetoxymethyl)cyclopropylidenemethyl]purine

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20 - 65℃; for 8h;	A 20% B 53%

ethyl bromoacetate (105-36-2) + 9H-purin-2-amine (452-06-2) → 2-(2-amino-9H-purin-9-yl)acetic acid (933477-63-5)

Conditions	Yield
Stage #1: 9H-purin-2-amine With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide for 2h; Inert atmosphere; Stage #3: With sodium hydroxide In water; N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	51%

(5aS,7S)-7-[(1R/S)-2-bromo-1-methylethyl]-3-methyl-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran (1134003-26-1) + 9H-purin-2-amine (452-06-2) → (5aS,7S)-7-[(1R/S)-2-(2-amino-9H-purin-9-yl)-1-methylethyl]-3-methyl-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran (1134003-03-4)

Conditions	Yield
Stage #1: 9H-purin-2-amine With caesium carbonate In N,N-dimethyl-formamide at 25℃; for 1h; Inert atmosphere; Stage #2: (5aS,7S)-7-[(1R/S)-2-bromo-1-methylethyl]-3-methyl-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran In N,N-dimethyl-formamide at 25℃; for 24h; Inert atmosphere;	48%

5-chloromethyl-2,2-dimethyl-1,3-dioxolane (4362-40-7) + 9H-purin-2-amine (452-06-2) → 9-(RS)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl-2-aminopurine (120139-11-9) + 7-(RS)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl-2-aminopurine (120139-12-0)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 14h;	A 44% B 15%

9H-purin-2-amine (452-06-2) + 2',3'-Dideoxyuridine (5983-09-5) → iso-2',3'-dideoxyadenosine (107550-74-3)

Conditions	Yield
at 50℃; for 2h; Escherichia coli JA-300 cells, pH 6.5;	44%

Diethyl 2-Bromoethoxymethanephosphonate (116384-57-7) + 9H-purin-2-amine (452-06-2) → [2-(2-Amino-purin-9-yl)-ethoxymethyl]-phosphonic acid diethyl ester (126354-35-6)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide a) At 80 deg C for 1 h 2) addition of IIc,80 deg C for 16 h;	40%

diethyl-2-(2-bromoethylidene)malonte (51385-79-6) + 9H-purin-2-amine (452-06-2) → 2-amino-9-(2,2-dicarboethoxycyclopropyl)purine (134470-59-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	39%

9H-purin-2-amine (452-06-2) + 5-(chloromethyl)-1,2,3-trimethoxybenzene (3840-30-0) → 9-(3,4,5-trimethoxybenzyl)-9H-purin-2-ylamine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 4h;	36%

9H-purin-2-amine (452-06-2) + 2-deoxy-2-fluoro-α-D-arabinofuranose 1-phosphate (850883-62-4) → 2-Amino-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine

Conditions	Yield
purine nucleoside phosphorylase In water at 50℃; for 216h; pH=7.5; Aqueous phosphate buffer; Enzymatic reaction;	32%

acetic anhydride (108-24-7) + 9H-purin-2-amine (452-06-2) → 2-(N-acetylamino)purine (23567-61-5)

Conditions	Yield
With ethanol 1) EtOH, 25 min, reflux, 2) 15 min, reflux; Yield given. Multistep reaction;

Upstream product

• 4394-85-8 4-morpholinecarboxaldehyde 
• 3546-50-7 pyrimidine-2,4,5-triamine 
• 77287-34-4 formamide 
• 14036-53-4 dimethoxymethyl acetate 
• 107550-74-3 iso-2',3'-dideoxyadenosine 
• 10310-21-1 2-Amino-6-chloropurin 
• 154-42-7 thioguanine 
• 3616-24-8 2-amino-9-(β-D-2'-deoxyribofuranosyl)-purine 
• 61991-08-0 amipurimycin 
• 33512-51-5 2-(methylthio)-9H-purine 

Downstream Products

• 2308-57-8 1,3-dihydro-2H-purin-2-one 
• 1598-61-4 2-fluoro-7(9)H-purine 
• 131266-15-4 7-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine 
• 104227-87-4 9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine 
• 107550-74-3 iso-2',3'-dideoxyadenosine 
• 109304-04-3 2-amino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine 
• 1598-61-4 2-fluoro-9H-purine 
• 1134003-03-4 (5aS,7S)-7-[(1R/S)-2-(2-amino-9H-purin-9-yl)-1-methylethyl]-3-methyl-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran 
• 84408-37-7 deoxyacyclovir 
• 4546-54-7 2?amino?9?(β?D?ribofuranosyl)purine 

Relevant articles and documents

Structure of amipurimycin, a nucleoside antibiotic having a novel branched sugar moiety

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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.

4'-substituted nucleosides

Nucleosides compounds of Formula I: STR1 wherein B is a purine or a pyrimidine; X and X' are H; Y is H; Y' is OH, F or H; or Y' and X' together makes a bond; Z is STR2 where n is zero, one, two or three; or Y' and Z together form a cyclic phosphate ester; Z' is --CN, --CH3, CH2 N3 or --CH2 J, where J is a halogen atom; or Z' and Y' together are --CH2 O--; and pharmaceutically acceptable esters, ethers, amides, N-acyl moieties and salts thereof.