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1076-22-8

Basic Information
CAS No.: 1076-22-8
Name: 1H-Purine-2,6-dione,3,9-dihydro-3-methyl-
Molecular Structure:
Molecular Structure of 1076-22-8 (1H-Purine-2,6-dione,3,9-dihydro-3-methyl-)
Formula: C6H6N4O2
Molecular Weight: 166.14
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;
EINECS: 214-058-1
Density: 1.54 g/cm3
Melting Point: >300 °C
Boiling Point: 322.4oC at 760 mmHg
Flash Point: 148.8oC
Solubility: Insoluble in water.
Appearance: white to cream solid
Hazard Symbols: HarmfulXn, VeryT+
Risk Codes: 22-26/27/28
Safety: 22-24/25
Transport Information:
PSA: 83.54000
LogP: -1.05010
Synthetic route
90801-87-9

4-(N-methylamino)-1H-imidazole-5-carboxamide

1076-22-8

3-methylxanthine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With acetic acid nachfolgenden Behandeln mit Eisenchlorid;
6972-82-3

5,6-diamino-1-methyluracil

1076-22-8

3-methylxanthine

6972-78-7

6-amino-1-methyl-5-nitrosouracil

1076-22-8

3-methylxanthine

Conditions
ConditionsYield
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

1076-22-8

3-methylxanthine

874495-58-6

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

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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With rat liver microsome; NADPH In phosphate buffer Enzyme kinetics; Further Variations:; inhibition by mexiletine and its metabolites; Oxidation;
3-methyl-8-chloro-xanthine

3-methyl-8-chloro-xanthine

1076-22-8

3-methylxanthine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
at 220℃;
6972-82-3

5,6-diamino-1-methyluracil

1076-22-8

3-methylxanthine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With dihydrogen peroxide at 20℃; for 0.133333h; pH=6; Kinetics; UV-irradiation;
6972-82-3

5,6-diamino-1-methyluracil

122-51-0

orthoformic acid triethyl ester

1076-22-8

3-methylxanthine

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

C6H8N4O4

1076-22-8

3-methylxanthine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sodium hydroxide In methanol; water90%
1076-22-8

3-methylxanthine

2550-36-9

(bromomethylcyclohexane)

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

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
at 110℃; for 1.5h; closed Kjeldahl flask;A 61%
B 28%
1076-22-8

3-methylxanthine

2163-00-0

1,6-dichlorohexane

125663-71-0

1,7-Bis(ω-chlorohexyl)-3-methyl-xanthine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
1076-22-8

3-methylxanthine

142-28-9

1,3-Dichloropropane

125663-68-5

1,7-Bis(γ-chloropropyl)-3-methyl-xanthine

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

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

Uses

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

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.

Safety Profile

Poison by intravenous route. Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic fumes of NOx.
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