2,6-Dihydroxy-3-methylpurine supplier

Name
2,6-Dihydroxy-3-methylpurine
EINECS 214-058-1
CAS No. 1076-22-8
Article Data49
CAS DataBase
Density 1.54 g/cm³
Solubility Insoluble in water.
Melting Point >300 °C
Formula C₆H₆N₄O₂
Boiling Point 322.4oC at 760 mmHg
Molecular Weight 166.139
Flash Point 148.8oC
Transport Information
Appearance white to cream solid
Safety 22-24/25
Risk Codes 22-26/27/28
Molecular Structure
Hazard Symbols Xn, T+
Synonyms 1H-Purine-2,6-dione,3,7-dihydro-3-methyl- (9CI);Xanthine, 3-methyl- (6CI,7CI,8CI);3-Methyl-3,7-dihydro-1H-purine-2,6-dione;3-Methyl-3,7-dihydropurine-2,6-dione;3-Methylxanthine;NSC 515466;
PSA 83.54000
LogP -1.05010

Synthetic route

: 90801-87-9
4-(N-methylamino)-1H-imidazole-5-carboxamide

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
With formic acid; perchloric acid adsorbed on silica gel In ethanol at 20℃; for 0.333333h; Solvent;	95.12%

: 64-18-6
formic acid

: 6972-82-3
5,6-diamino-1-methyluracil

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
Stage #1: formic acid; 5,6-diamino-1-methyluracil In water at 105℃; for 3h; Stage #2: With sodium hydroxide In water at 105℃; for 1h;	94.1%
Stage #1: formic acid; 5,6-diamino-1-methyluracil In water for 3h; Reflux; Inert atmosphere; Stage #2: With sodium hydroxide In water for 1h; Reflux; Inert atmosphere;	80%
Stage #1: formic acid; 5,6-diamino-1-methyluracil In water for 3h; Reflux; Inert atmosphere; Stage #2: With sodium hydroxide In water at 20℃; for 1h; Inert atmosphere; Reflux;	78%

: 56025-86-6
7-benzyl-3-methylxanthine

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
With 20 % Pd(OH)2/C; hydrogen In acetic acid; ethyl acetate at 90℃; under 75007.5 Torr; for 0.416667h; H-Cube reactor;	90%

: 3080-28-2
3-methylxanthine

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
With hydrogenchloride In water for 0.5h; Ambient temperature;	84%
With hydrogenchloride In water at 25℃; Rate constant; hydrolytic cleavage of the glycosidic bond in several HCl solutions;

: 50996-13-9
1-methyl-2,4-dioxo-5,6-diaminopyrimidine hydrochloride

: 122-51-0
orthoformic acid triethyl ester

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 70℃; for 3.5h;	53%

: 50-00-0
formaldehyd

: 6972-82-3
5,6-diamino-1-methyluracil

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
With acetic acid nachfolgenden Behandeln mit Eisenchlorid;

: 6972-82-3
5,6-diamino-1-methyluracil

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 1076-22-8
3-methylxanthine

: 6972-78-7
6-amino-1-methyl-5-nitrosouracil

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
With palladium on activated charcoal; formic acid; isopropyl alcohol Erwaermen des Reaktionsprodukts mit wss.NaOH;
Multi-step reaction with 3 steps 1: 98 percent / H2 / 10percent Pd/C / H2O / 3750.3 Torr / Ambient temperature 2: 96 percent / 10percent Pd/C / 39.9 °C 3: NaOH View Scheme
Multi-step reaction with 2 steps 1: Na2S2O4, 25percent aq. NH4OH / 20 - 50 °C 2: 2.) 2.2 M aq. NaOH / 1.) reflux, 2 h, 2.) reflux, 45 min View Scheme

: 10184-42-6
5-acetylamino-6-amino-1-methyl-1H-pyrimidine-2,4-dione

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 1076-22-8
3-methylxanthine

: 874495-58-6
(1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amidosulfuric acid

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 1076-22-8
3-methylxanthine

: 64-18-6
formic acid

: 6972-78-7
6-amino-1-methyl-5-nitrosouracil

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
1.) electrolyse: formamide, platinum mesh as anode, tin plate as cathode, 30-35 deg C, current density 12.5 A/dm2, 2.) 180-200 deg C; Yield given. Multistep reaction;

: 83-67-0
theobromine /

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
With sodium thiophenolate at 280℃; for 1.5h; Yield given;

: 14785-95-6
3-methyl-4-amino-5-formylamino-2,6-dioxypyrimidine

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
With sodium hydroxide

: 58-55-9
theophylline

A: 6136-37-4
1-methylxanthine

B: 1076-22-8
3-methylxanthine

C: 944-73-0
1,3-dimethyluric acid

Conditions

Conditions	Yield
With rat liver microsome; NADPH In phosphate buffer Enzyme kinetics; Further Variations:; inhibition by mexiletine and its metabolites; Oxidation;

...Expand

3-methyl-8-chloro-xanthine: 3-methyl-8-chloro-xanthine

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
With phosphonium iodide; hydrogen iodide
With phosphonium iodide; hydrogen iodide

3-methyl-xanthine-carboxylic acid-(8): 3-methyl-xanthine-carboxylic acid-(8)

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
at 260℃;

sodium salt of 3-methyl-4-amino-formylamino-uracil: sodium salt of 3-methyl-4-amino-formylamino-uracil

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
at 220℃;

: 6972-82-3
5,6-diamino-1-methyluracil

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / 10percent Pd/C / 39.9 °C 2: NaOH View Scheme

: 81812-69-3
1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5-<(ethoxycarbonyl)methylamino>imidazole-4-carboxamide

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / 1N NaOH / H2O / 3 h / Ambient temperature 2: 0.1N HCl / H2O / 25 °C / hydrolytic cleavage of the glycosidic bond in several HCl solutions View Scheme

: 68768-26-3
1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5-(methylamino)imidazole-4-carboxamide

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 36 percent / AcONa / acetic acid / 5 h / 30 °C 2: 69 percent / 1N NaOH / H2O / 3 h / Ambient temperature 3: 0.1N HCl / H2O / 25 °C / hydrolytic cleavage of the glycosidic bond in several HCl solutions View Scheme

: 58-55-9
theophylline

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 10 percent / sodium thiophenolate / 1.5 h / 280 °C 2: sodium thiophenolate / 1.5 h / 280 °C View Scheme

: 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 37 percent / sodium thiophenolate / 1.5 h / 250 °C 2: 10 percent / sodium thiophenolate / 1.5 h / 280 °C 3: sodium thiophenolate / 1.5 h / 280 °C View Scheme
Multi-step reaction with 2 steps 1: 21 percent / sodium thiophenolate / 1.5 h / 250 °C 2: sodium thiophenolate / 1.5 h / 280 °C View Scheme

: 2434-53-9
6-amino-1-methyluracil

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: NaNO2, AcOH / H2O / 2 h / Ambient temperature 2: Na2S2O4, 25percent aq. NH4OH / 20 - 50 °C 3: 2.) 2.2 M aq. NaOH / 1.) reflux, 2 h, 2.) reflux, 45 min View Scheme
Multi-step reaction with 3 steps 1.1: acetic acid; sodium nitrite / water / 1.5 h / 20 - 50 °C 2.1: ammonium hydroxide; sodium dithionite / 7 h / 25 - 60 °C 3.1: water / 3 h / 105 °C 3.2: 1 h / 105 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium dithionite; ammonium hydroxide / 1 h / 50 °C 2.1: water / 3 h / Reflux; Inert atmosphere 2.2: 1 h / Reflux; Inert atmosphere View Scheme

: 58-55-9
theophylline

A: 3240-72-0
5,6-diaminouracil

B: 1076-22-8
3-methylxanthine

C: 127091-92-3
1,3-dimethyluric acid

D: 1-methylxanthine

E: 1-methyluric acid

F: 3-methyluric acid

G: 3-methyltetrahydro-1H-purine-2,6-dione

H: 1-methyltetrahydro-1H-purine-2,6-dione

I: 69-89-6
xanthin

Conditions

Conditions	Yield
With dihydrogen peroxide at 20℃; for 0.133333h; pH=6; Kinetics; UV-irradiation;

...Expand

: 6972-82-3
5,6-diamino-1-methyluracil

: 122-51-0
orthoformic acid triethyl ester

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 70℃; for 3.5h; Inert atmosphere;

: C6H8N4O4

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
With sodium hydroxide In water at 70 - 95℃; for 1h; pH=1.5; pH-value; Temperature;

: 6972-77-6
N-cyanoacetyl-N'-methyl-urea

: 1076-22-8
3-methylxanthine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 0.5 h / 95 °C / pH 8 2.1: sodium nitrite / 2.5 h / 20 °C / pH 8 2.2: 3 h / 50 °C 3.1: sodium hydroxide / water / 1 h / 70 - 95 °C / pH 1.5 View Scheme

: 1076-22-8
3-methylxanthine

: 93703-24-3
3-methyl-8-bromoxanthine

Conditions

Conditions	Yield
With bromine; sodium acetate In acetic acid at 50 - 65℃; for 3h;	96.6%
With bromine; acetic acid at 100℃; for 6h;	95%
With bromine; sodium acetate; acetic acid at 65℃; for 3h;	94.17%

: 1076-22-8
3-methylxanthine

: 61493-85-4
but-2-yn-1-yl methanesulfonate

: 7-but-2-ynyl-3-methyl-3,7-dihydro-purine-2,6-dione

Conditions

Conditions	Yield
With potassium hydrogencarbonate In 1-methyl-pyrrolidin-2-one at 50℃; for 7.75h;	94%

: 1076-22-8
3-methylxanthine

: 77-78-1
dimethyl sulfate

: 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions

Conditions	Yield
With tetramethyl ammoniumhydroxide; potassium carbonate In methanol; water at 65 - 70℃;	92.5%

: 1076-22-8
3-methylxanthine

: 75-03-6
ethyl iodide

: 54889-96-2
1,7-diethyl-3-methylxanthine

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 4h;	92%

: 1076-22-8
3-methylxanthine

: 824-94-2
p-methoxybenzyl chloride

: 143958-73-0
3,7-dihydro-7-(4-methoxybenzyl)-3-methyl-1H-purine-2,6-dione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 2h;	90%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1.5h;

: 1076-22-8
3-methylxanthine

: 56395-72-3
7-(6-hydroxy-hexyl)-3-methyl-3,7-dihydro-purine-2,6-dione

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water	90%

: 1076-22-8
3-methylxanthine

: 2550-36-9
(bromomethylcyclohexane)

: 7-(cyclohexylmethyl)-3-methyl-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
Stage #1: 3-methylxanthine With sodium hydride In dimethyl sulfoxide; mineral oil at 0 - 80℃; for 0.5h; Stage #2: Cyclohexylmethyl bromide In dimethyl sulfoxide; mineral oil at 80℃; for 12h; Inert atmosphere;	89%

: 1076-22-8
3-methylxanthine

: 100-39-0
benzyl bromide

: 56025-86-6
7-benzyl-3-methylxanthine

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 60℃; for 12h;	88%
In methanol; sodium hydroxide; water
In methanol; sodium hydroxide; water

: 1076-22-8
3-methylxanthine

: 77-78-1
dimethyl sulfate

: 83-67-0
theobromine /

Conditions

Conditions	Yield
Stage #1: 3-methylxanthine; dimethyl sulfate With sodium hydrogencarbonate In water; acetone at 55 - 60℃; for 4h; Stage #2: With hydrogenchloride In water at 80℃; pH=5 - 6; Product distribution / selectivity;	87%

: 75-30-9
2-iodo-propane

: 1076-22-8
3-methylxanthine

: 1,7-diisopropyl-3-methylxanthine

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 4h;	87%

: 1076-22-8
3-methylxanthine

: 75-03-6
ethyl iodide

: 55242-68-7
3-methyl-7-ethyl-xanthine

Conditions

Conditions	Yield
Stage #1: 3-methylxanthine With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 0.5h; Stage #2: ethyl iodide In N,N-dimethyl-formamide for 5h;	86%

: 1076-22-8
3-methylxanthine

: 629616-88-2
2-chloro-N-(2-(6-bromo)pyridinyl)acetamide

: N-(6-bromopyridin-2-yl)-2-(3-methyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)acetamide

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	83.7%

: 1076-22-8
3-methylxanthine

: 93703-23-2
3-methyl-8-nitroxanthine

Conditions

Conditions	Yield
With nitric acid In acetic acid at 120℃; for 1.5h;	83%
With nitric acid; acetic acid 1.) 100 deg C, 30 min, 2.) reflux, 15 min;	63%

: 1076-22-8
3-methylxanthine

: 2-chloro-N-(2-(6-methyl-5-(trifluoromethyl)pyridin-3-yl)-1,3-thiazol-4-yl)acetamide

: 2-(3-methyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)-N-(2-(6-methyl-5-(trifluoromethyl)pyridin-3-yl)-1,3-thiazol-4-yl)acetamide

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 50℃; for 2h; Inert atmosphere;	83%

: 1076-22-8
3-methylxanthine

: 1699-59-8
3,4-dibenzyloxybenzyl chloride

: C48H42N4O6

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide at 60℃; for 12h;	78%
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide at 60℃; for 12h;	78%

: 1076-22-8
3-methylxanthine

A: 120642-74-2
3-methyl-7-aminoxanthine

B: 120642-75-3
3-methyl-1,7-diaminoxanthine

Conditions

Conditions	Yield
With potassium hydroxide; sodium hydrogencarbonate; hydroxylamine-O-sulfonic acid In water at 50 - 60℃; for 0.666667h;	A 67% B 7%
With potassium hydroxide; sodium hydrogencarbonate; hydroxylamine-O-sulfonic acid In water at 50℃; for 0.166667h;	A 67% B 7%

: 1076-22-8
3-methylxanthine

: 74-88-4
methyl iodide

A: 83-67-0
theobromine /

B: 86180-33-8
1,7,9-trimethylxanthinium iodide

Conditions

Conditions	Yield
at 110℃; for 1.5h; closed Kjeldahl flask;	A 61% B 28%

...Expand

: 1076-22-8
3-methylxanthine

: 2163-00-0
1,6-dichlorohexane

: 125663-71-0
1,7-Bis(ω-chlorohexyl)-3-methyl-xanthine

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 85 - 105℃;	60%

: 628-76-2
1,5-dichloropentane

: 1076-22-8
3-methylxanthine

: 125663-70-9
1,7-Bis(ω-chloropentyl)-3-methyl-xanthine

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 85 - 105℃;	58%

: 1076-22-8
3-methylxanthine

: 110-56-5
1,4-dichlorobutane

: 125663-69-6
1,7-Bis(ω-chlorobutyl)-3-methyl-xanthine

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 85 - 105℃;	55%

: 1076-22-8
3-methylxanthine

: 105-36-2
ethyl bromoacetate

: ethyl 2-(3-methyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)acetate

Conditions

Conditions	Yield
Stage #1: 3-methylxanthine With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 3h; Inert atmosphere; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 20℃; for 19h;	55%

: 55401-97-3
2-(Bromomethyl)pyridine

: 1076-22-8
3-methylxanthine

: N-(2-bromo-1,3-thiazol-4-yl)-2-chloroacetamide

: N-(2-bromo-1,3-thiazol-4-yl)-2-(3-methyl-2,6-dioxo-1-(pyridin-2-ylmethyl)-2,3-dihydro-1H-purin-7(6H)-yl)acetamide

Conditions

Conditions	Yield
Stage #1: 3-methylxanthine; N-(2-bromo-1,3-thiazol-4-yl)-2-chloroacetamide With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Stage #2: 2-(Bromomethyl)pyridine With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2h; Inert atmosphere;	54%

...Expand

: 1076-22-8
3-methylxanthine

: 142-28-9
1,3-Dichloropropane

: 125663-68-5
1,7-Bis(γ-chloropropyl)-3-methyl-xanthine

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 85 - 105℃;	53%

: 542-69-8
1-iodo-butane

: 1076-22-8
3-methylxanthine

: 55242-69-8
7-butyl-3-methyl-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
Stage #1: 3-methylxanthine With potassium hydroxide In methanol; water at 80℃; for 1.5h; Stage #2: 1-iodo-butane In methanol; water at 50℃; for 24h;	52%

: 2162-98-3
1,10-dichlorodecane

: 1076-22-8
3-methylxanthine

: 125663-72-1
1,7-Bis(ω-chlorodecyl)-3-methyl-xanthine

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 85 - 105℃;	51%

2,6-Dihydroxy-3-methylpurine Chemical Properties

IUPAC Name: 2,6-Dihydroxy-3-methylpurine
The MF of 2,6-Dihydroxy-3-methylpurine (1076-22-8) is C₆H₆N₄O₂.

The MW of 2,6-Dihydroxy-3-methylpurine (1076-22-8) is 166.14.
Synonyms of 2,6-Dihydroxy-3-methylpurine (1076-22-8): 3-Methylxanthine ; 1H-purine-2,6-dione, 3,7-dihydro-3-methyl- ; 3-Methyl-3,7-dihydro-1H-purin-2,6-dion
Product Categories: Pyridines,Purines and Pteredines;Heterocycles series
Form: White to yellow powder or solid
Index of Refraction: 1.626
EINECS: 214-058-1
Density: 1.539 g/ml
Melting Point: >300 °C
Storage temp: 2-8°C

2,6-Dihydroxy-3-methylpurine Uses

The MF of 2,6-Dihydroxy-3-methylpurine (1076-22-8) is used for propentofylline (cognition enhancer).

2,6-Dihydroxy-3-methylpurine Toxicity Data With Reference

1.	ipr-mus LD50:1300 mg/kg	FATOAO Farmakologiya i Toksikologiya (Moscow). 46 (5)(1983),104.
2.	ivn-dog LDLo:300 mg/kg	AEXPBL Archiv fuer Experimentelle Pathologie und Pharmakologie. 43 (1900),305.
3.	ivn-rbt LDLo:500 mg/kg	AEXPBL Archiv fuer Experimentelle Pathologie und Pharmakologie. 43 (1900),305.

2,6-Dihydroxy-3-methylpurine Safety Profile

Poison by intravenous route. Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic fumes of NO_x.
Safety information of 2,6-Dihydroxy-3-methylpurine (1076-22-8):
Hazard Codes Xn,T+
Risk Statements
22 Harmful if swallowed
26/27/28 Very Toxic by inhalation, in contact with skin and if swallowed
Safety Statements
22 Do not breathe dust
24/25 Avoid contact with skin and eyes
WGK Germany 1
RTECS ZD8750000

Product Name

2,6-Dihydroxy-3-methylpurine

Synthetic route

2,6-Dihydroxy-3-methylpurine Chemical Properties

2,6-Dihydroxy-3-methylpurine Uses

2,6-Dihydroxy-3-methylpurine Toxicity Data With Reference

2,6-Dihydroxy-3-methylpurine Safety Profile

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