16526-56-0

Basic information

• Product Name: 2-methyladenosine
• Synonyms: 2-methyladenosine;Adenosine, 2-Methyl-
• CAS NO: 16526-56-0
• Molecular Formula: C₁₁H₁₅N₅O₄
• Molecular Weight: 281.27
• Mol File: 16526-56-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 517.8°Cat760mmHg
• Flash Point: 266.9°C
• Appearance: /
• Density: 1.96g/cm³
• Vapor Pressure: 1.51E-11mmHg at 25°C
• Refractive Index: 1.856
• PKA: 13.12±0.70(Predicted)
• CAS DataBase Reference: 2-methyladenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyladenosine(16526-56-0)
• EPA Substance Registry System: 2-methyladenosine(16526-56-0)

Safety Data

• Hazardous Substances Data: 16526-56-0(Hazardous Substances Data)

Usage

Definition

ChEBI: A methyladenosine in which the methyl group is located at position 2 on the adenine ring.

InChI:InChI=1/C11H15N5O4/c1-4-14-9(12)6-10(15-4)16(3-13-6)11-8(19)7(18)5(2-17)20-11/h3,5,7-8,11,17-19H,2H2,1H3,(H2,12,14,15)/t5-,7-,8-,11-/m1/s1

Synthetic route

5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carbonitrile (23192-64-5) → 2-methyladenosine (16526-56-0)

Conditions	Yield
In ammonia methyl alcohol; acetonitrile	35.9%

acetic anhydride (108-24-7) + 2-methyl-6-aminopurine (1445-08-5) → 2-methyladenosine (16526-56-0)

Conditions	Yield
Behandeln des Reaktionsprodukts mit wss.NaOH und HgCl2 in Aethanol, Erhitzen der entstandenen Chloromercurio-Verb. mit Tri-O-acetyl-α-D-ribofuranosylchlorid in Xylol und anschlissenden Behandeln mit methanol.NH3;

trimethylaluminum (75-24-1) + 2-Bromo-adenosine (146-76-9) → 2-methyladenosine (16526-56-0)

Conditions	Yield
Yield given. Multistep reaction;

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-amino-2-methyl-purin-9-yl)-tetrahydro-furan-3-yl ester → 2-methyladenosine (16526-56-0)

Conditions	Yield
With ammonia In methanol
With potassium carbonate In methanol at 23℃; for 12h;

tert-butyl peroxyacetate (107-71-1) + adenosine (58-61-7) → 8-methyladenosine (56973-12-7) + 2-methyladenosine (16526-56-0) + N6-methyladenosine (1867-73-8)

Conditions	Yield
at 32℃; for 20h; Product distribution; Mechanism; Irradiation; solutions of pH 1.4-12.4;

N-(4,6-diamino-2-methyl-pyrimidin-5-yl)-formamide → 2-methyladenosine (16526-56-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: formamide 2: Behandeln des Reaktionsprodukts mit wss.NaOH und HgCl2 in Aethanol, Erhitzen der entstandenen Chloromercurio-Verb. mit Tri-O-acetyl-α-D-ribofuranosylchlorid in Xylol und anschlissenden Behandeln mit methanol.NH3 View Scheme

2-methyl-5-phenylazo-pyrimidine-4,6-diyldiamine (5473-05-2) → 2-methyladenosine (16526-56-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: palladium/charcoal; water / Hydrogenation 2: formamide 3: Behandeln des Reaktionsprodukts mit wss.NaOH und HgCl2 in Aethanol, Erhitzen der entstandenen Chloromercurio-Verb. mit Tri-O-acetyl-α-D-ribofuranosylchlorid in Xylol und anschlissenden Behandeln mit methanol.NH3 View Scheme

trimethylaluminum (75-24-1) + 2-iodoadenosine (35109-88-7) → 2-methyladenosine (16526-56-0)

Conditions	Yield
Stage #1: 2-iodoadenosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane at 80℃; Stage #2: trimethylaluminum; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; hexanes at 68℃; for 3.66h; Stage #3: With water; ammonium chloride In methanol at 65℃; for 3h;

C20H39N5O4Si3 (53293-86-0) → 2-methyladenosine (16526-56-0)

Conditions	Yield
With water; ammonium chloride In methanol

2-methyladenosine (16526-56-0) → α-D-ribofuranosyl-1-phosphate (18646-11-2) + 2-methyladenine (1445-08-5)

Conditions	Yield
With E. coli purine nucleoside phosphorylase Enzyme kinetics; Substitution;

2-methyladenosine (16526-56-0) → C11H14ClN5O3 (1172119-93-5)

Conditions	Yield
With thionyl chloride In acetonitrile at 0℃;

Upstream product

• 108-24-7 acetic anhydride 
• 1445-08-5 2-methyl-6-aminopurine 
• 53293-86-0 C₂₀H₃₉N₅O₄Si₃ 
• 75-24-1 trimethylaluminum 
• 35109-88-7 2-iodoadenosine 
• 23192-64-5 5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carbonitrile 
• 5473-05-2 2-methyl-5-phenylazo-pyrimidine-4,6-diyldiamine 
• 107-71-1 tert-butyl peroxyacetate 
• 58-61-7 adenosine 
• 146-76-9 2-Bromo-adenosine 

Downstream Products

• 18646-11-2 α-D-ribofuranosyl-1-phosphate 
• 1445-08-5 2-methyladenine 

Relevant articles and documents

Convenient Method for the Synthesis of C-Alkylated Purine Nucleosides: Palladium-Catalyzed Cross-Coupling Reaction of Halogenopurine Nucleosides with Trialkylaluminums

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Isolation and characterization of 2-methyladenosine from Escherichia coli tRNA Glu 2 , tRNA Asp 1 , tRNA His 1 and tRNA Arg .

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Discovery of new S-adenosylmethionine decarboxylase inhibitors for the treatment of Human African Trypanosomiasis (HAT)

Modification of the structure of trypanosomal AdoMetDC inhibitor 1 (MDL73811) resulted in the identification of a new inhibitor 7a, which features a methyl substituent at the 8-position. Compound 7a exhibits improved potencies against both the trypanosomal AdoMetDC enzyme and parasites, and better blood brain barrier penetration than 1.

Antiviral Activity of C-Alkylated Purine Nucleosides Obtained by Cross-Coupling with Tetraalkyltin Reagents

2-, 6-, And 8-alkylated (methyl, ethyl, and vinyl) adenosine analogues were synthesized by a palladium-catalyzed cross-coupling of a tetraalkyltin with the halogenated purine nucleosides.The synthesis of the 8-substituted analogues was accomplished using a transient protection procedure.The 6-alkylated-9-β-D-ribofuranosylpurines as well as 2-ethyladenosine were cytotoxic at relatively low concentrations (0.8-10 μg/mL). 8-Methyladenosine was a potent and selective inhibitor of vaccinia virus, whereas 8-ethyl- and 8-vinyladenosine were specifically inhibitory to respiratory syncytial virus. 8-Vinyladenosine displayed particular activity against herpes simplex virus (type 1).