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Basic Information

Molecular Structure:
CAS No.:	106941-25-7
Name:	Adefovir
Article Data:	21

Formula:	C₈H₁₂N₅O₄P
Molecular Weight:	273.188
Synonyms:	((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)phosphonic acid;9-(2-Phosphorylmethoxyethyl)adenine;PMEA;Adefovir [USAN:INN];2-(6-aminopurin-9-yl)ethoxymethylphosphonic acid;N-(2-Phophonomethoxyethyl-2,6-diaminopurine);GS 0393;GS 393;9-(2-(Phosphonomethoxy)ethyl)adenine;Phosphonic acid, ((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)-;9-[2-Phosphonylmethoxyethyl]adenine;9-[2-(Phosphonomethoxy)ethyl]adenine (PMEA);9-[2-phosphonyl methoxyethyl]adenine;Adefovir dipivox;9-[2-(phosphonomethoxy)ethyl]adenine;[[2-(6-amino-9H-purin-9-yl) ethoxy] methyl] phosphonic acid;9-(2-phosphonyl methoxyethyl)adenine;Adefovir Dipivozil;9-(2-Phosphonylmethoxyethyl)adenine;
EINECS:	600-789-7
Density:	1.88 g/cm³
Melting Point:	>260 °C
Boiling Point:	632.5 °C at 760 mmHg
Flash Point:	336.3 °C
Appearance:	white to off-white powder
Hazard Symbols:	T
Risk Codes:	25
Safety:	45
PSA:	146.19000
LogP:	0.14150

Synthetic route

: 116384-53-3
[[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester

: 106941-25-7
Adefovir

Conditions

Conditions	Yield
With trimethylsilyl bromide	95%
Stage #1: [[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester With trimethylsilyl bromide In acetonitrile at 20℃; for 3h; Large scale; Stage #2: With sodium hydroxide In water for 2h; Reflux; Large scale;	86.3%
With hydrogen bromide In water at 90℃; for 5h; Temperature; Time;	86%

: 142340-94-1
[2-(6-Amino-purin-9-yl)-ethoxymethyl]-phosphonic acid diisopropyl ester

: 106941-25-7
Adefovir

Conditions

Conditions	Yield
With hydrogenchloride In water at 140℃; for 0.166667h; Microwave irradiation; Sealed tube;	95%
Multi-step reaction with 2 steps 1: acetonitrile 2: aq. NH3 View Scheme

: 107021-27-2
Methyl Ester of 9-(2-Phosphonylmethoxyethyl)adenine

: 106941-25-7
Adefovir

Conditions

Conditions	Yield
With trimethylsilyl iodide; triethylamine carbonate 1) DMF, R.T., 16 h 2) 80 deg C; Yield given. Multistep reaction;

: 31618-90-3
diethyl (p-toluenesulfonyloxymethane)phosphonate

: 707-99-3
9-(2-hydroxyethyl)adenine

: 106941-25-7
Adefovir

Conditions

Conditions	Yield
With trimethylsilyl bromide; sodium t-butanolate 1.) DMF; Yield given. Multistep reaction;

: C14H28N5O4PSi2

: 106941-25-7
Adefovir

Conditions

Conditions	Yield
With ammonium hydroxide Yield given;
With water	33.0 g

: 212894-84-3
[2-(5-Amino-6-chloro-pyrimidin-4-ylamino)-ethoxymethyl]-phosphonic acid diethyl ester

: 106941-25-7
Adefovir

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / 3 h / 120 °C 2: 87 percent / NH3 liquid / tetrahydrofuran; dimethylsulfoxide / 24 h / 25 °C 3: 95 percent / TMSBr View Scheme

: 185900-69-0
O,O-diethyl((2-(6-chloro-9H-purin-9-yl)ethoxy)methyl)phosphonate

: 106941-25-7
Adefovir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / NH3 liquid / tetrahydrofuran; dimethylsulfoxide / 24 h / 25 °C 2: 95 percent / TMSBr View Scheme

: 55343-28-7
9-(2-Hydroxyethyl)-N6-benzoyladenine

: 106941-25-7
Adefovir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) NaH 2) 0.5 mol l-1 NaOH / 1)DMF, R.T., 48 h, 2) 50 deg C, 6 h 2: 1) iodotrimethylsilane 2) 2 mol l-1 triethylammonium hydrogen carbonate / 1) DMF, R.T., 16 h 2) 80 deg C View Scheme

: 707-99-3
9-(2-hydroxyethyl)adenine

: 106941-25-7
Adefovir

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / chlorotrimethylsilane / pyridine 2: 1) NaH 2) 0.5 mol l-1 NaOH / 1)DMF, R.T., 48 h, 2) 50 deg C, 6 h 3: 1) iodotrimethylsilane 2) 2 mol l-1 triethylammonium hydrogen carbonate / 1) DMF, R.T., 16 h 2) 80 deg C View Scheme
Multi-step reaction with 2 steps 1: 1) NaH, 2) 0.5 mol l-1 NaOH / 1) DMF, R.T., 48 h, 2) 50 deg C, 6 h 2: 1) iodotrimethylsilane 2) 2 mol l-1 triethylammonium hydrogen carbonate / 1) DMF, R.T., 16 h 2) 80 deg C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 5 °C / Large scale 1.2: 5 h / 5 °C / Large scale 2.1: trimethylsilyl bromide / acetonitrile / 3 h / 20 °C / Large scale 2.2: 2 h / Reflux; Large scale View Scheme
Multi-step reaction with 2 steps 1: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 12 h / 80 °C 2: chloro-trimethyl-silane / chlorobenzene / 10 h / 120 °C View Scheme
Multi-step reaction with 2 steps 1.1: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 1 h / 78 - 82 °C 1.2: 78 - 82 °C 2.1: trimethylsilyl bromide / 80 - 85 °C View Scheme

: 9-(2-Diethoxyphosphonomethoxyethyl)adenine

: 2857-97-8
trimethylsilyl bromide

: 106941-25-7
Adefovir

Conditions

Conditions	Yield
In dichloromethane; water; acetone

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Chemistry

Molecular Structure of 9-(2-Phosphonylmethoxyethyl)adenine (CAS NO.106941-25-7):

Molecular Formula: C₈H₁₂N₅O₄P
Molecular Weight: 273.1857
IUPAC Name: 2-(6-Aminopurin-9-yl)ethoxymethylphosphonic acid
Synonyms of 9-(2-Phosphonylmethoxyethyl)adenine (CAS NO.106941-25-7): Adefovir [USAN:INN] ; ((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)phosphonic acid ; 9-(2-(Phosphonomethoxy)ethyl)adenine ; Adefovir ; BRN 3561094 ; DRG-0156 ; GS 0393 ; GS 393 ; GS-0393 ; N-(2-Phophonomethoxyethyl-2,6-diaminopurine) ; N-(2-Phosphonylmethoxyethyl)adenine ; PMEA ; Phosphonic acid, ((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)- ; UNII-6GQP90I798
CAS NO: 106941-25-7
Classification Code: Anti-Infective Agents ; Anti-Retroviral Agents ; Antiviral ; Antiviral agents ; Enzyme Inhibitors ; Mutation data ; Nucleic Acid Synthesis Inhibitors ; Reverse Transcriptase Inhibitors
Melting point: >260°C
Index of Refraction: 1.768
Molar Refractivity: 60.14 cm³
Molar Volume: 144.9 cm³
Surface Tension: 103.8 dyne/cm
Density: 1.88 g/cm³
Flash Point: 336.3 °C
Enthalpy of Vaporization: 98.29 kJ/mol
Boiling Point: 632.5 °C at 760 mmHg
Vapour Pressure: 7.24E-17 mmHg at 25°C

Uses

9-(2-Phosphonylmethoxyethyl)adenine (CAS NO.106941-25-7) can be used for antiviral.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD	intravenous	> 1gm/kg (1000mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Antimicrobial Agents and Chemotherapy. Vol. 40, Pg. 1072, 1996.
mouse	LDLo	intraperitoneal	1600mg/kg (1600mg/kg)		Antimicrobial Agents and Chemotherapy. Vol. 40, Pg. 1072, 1996.

Safety Profile

Mutation data reported. When heated to decomposition it emits toxic vapors of NO_x and PO_x.

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