Product Name

  • Name

    8-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-7-methyl-purine-2,6 -dione

  • EINECS
  • CAS No. 155270-99-8
  • Article Data20
  • CAS DataBase
  • Density 1.243 g/cm3
  • Solubility
  • Melting Point 191 °C
  • Formula C20H24N4O4
  • Boiling Point 600.991 °C at 760 mmHg
  • Molecular Weight 384.435
  • Flash Point 317.268 °C
  • Transport Information
  • Appearance
  • Safety 45
  • Risk Codes 25
  • Molecular Structure Molecular Structure of 155270-99-8 (8-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-7-methyl-purine-2,6 -dione)
  • Hazard Symbols T
  • Synonyms 1H-Purine-2,6-dione,8-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-3,7-dihydro-7-methyl-, (E)-;KW 6002;Istradefylline [USAN:INN];1H-Purine-2,6-dione,8-[(1E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-3,7-dihydro-7-methyl-;(E)-8-(3,4-Dimethoxystyryl)-1,3-diethyl-7-methylxanthine;8-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-7-methyl-3,7-dihydro-1H-purine-2,6-dione;UNII-2GZ0LIK7T4;
  • PSA 80.28000
  • LogP 2.12410

Synthetic route

8-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
155270-98-7

8-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

methyl iodide
74-88-4

methyl iodide

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 5h;99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;95%
1,3-diethyl-7-methyl-1H-purine-2,6(3H,7H)-dione
31617-39-7

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

3,4-dimethoxystyrene
6380-23-0

3,4-dimethoxystyrene

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
Stage #1: 1,3-diethyl-7-methyl-1H-purine-2,6(3H,7H)-dione With pyridine; palladium diacetate; copper(II) acetate monohydrate; copper(l) chloride In N,N-dimethyl acetamide at 20℃; for 0.0833333h; Heck reaction; Inert atmosphere;
Stage #2: 3,4-dimethoxystyrene In N,N-dimethyl acetamide at 120℃; for 20h; Heck reaction; Inert atmosphere;		95%
C20H26N4O5

C20H26N4O5

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
With sodium methylate In 1,4-dioxane at 90 - 95℃; for 3h; Reagent/catalyst; Temperature;94%
methyl 2‐cyano‐2‐[(2E)‐3‐(3,4‐dimethoxyphenyl)‐N‐methylprop‐2‐enamido]acetate

methyl 2‐cyano‐2‐[(2E)‐3‐(3,4‐dimethoxyphenyl)‐N‐methylprop‐2‐enamido]acetate

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
With N,N'-diethylurea In 1,4-dioxane at 90 - 95℃; for 4h;92.5%
1,3-diethyl-7,8-dimethyl-1H-purine-2,6-(3H,7H)-dione

1,3-diethyl-7,8-dimethyl-1H-purine-2,6-(3H,7H)-dione

3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
With acetic anhydride; acetic acid at 110℃; for 10h;92%
N,N'-diethylurea
623-76-7

N,N'-diethylurea

(E)-3,4-dimethoxycinnamic chloride
39856-08-1, 141236-46-6

(E)-3,4-dimethoxycinnamic chloride

ethyl 2-methylaminocyanoacetate

ethyl 2-methylaminocyanoacetate

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
Stage #1: N,N'-diethylurea; ethyl 2-methylaminocyanoacetate In 1,4-dioxane at 95 - 100℃; for 5h;
Stage #2: With potassium hydroxide at 10 - 95℃; for 3h;
Stage #3: (E)-3,4-dimethoxycinnamic chloride With triethylamine In 1,4-dioxane at 10 - 45℃; for 5h; Temperature;		90.9%
...Expand
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

8-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
155270-98-7

8-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 135℃; for 6h; Reagent/catalyst; Temperature; Molecular sieve;86%
With potassium tert-butylate In N,N-dimethyl-formamide at 135℃; for 6h; Reagent/catalyst; Temperature; Molecular sieve;86%
dimethyl sulfate
77-78-1

dimethyl sulfate

8-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
155270-98-7

8-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Darkness;71.8%
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

(E)-N-(6-amino-1,3-diethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(3,4-dimethoxyphenyl)propenamide
187393-68-6

(E)-N-(6-amino-1,3-diethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(3,4-dimethoxyphenyl)propenamide

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
Stage #1: (E)-N-(6-amino-1,3-diethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(3,4-dimethoxyphenyl)propenamide With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 0.5h;
Stage #2: carbonic acid dimethyl ester In N,N-dimethyl-formamide at 120 - 140℃; for 2h; Temperature;		52.4%
5,6-diamino-1,3-diethyluracil
52998-22-8

5,6-diamino-1,3-diethyluracil

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 65 percent / pyridine / CH2Cl2 / 16 h / 20 °C
2: 92 percent / 1,1,1,3,3,3-hyxamethyldisilazane; (NH4)2SO4 / 4 h / 170 - 180 °C
3: 95 percent / potassium carbonate / dimethylformamide / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: EDAC / dioxane; H2O
1.2: 35 percent / aq. NaOH / Heating
2.1: K2CO3 / dimethylformamide
View Scheme
Multi-step reaction with 2 steps
1: 1) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, 2) 1N NaOH / 1) dioxane, H2O, 2) dioxane, H2O, reflux
2: K2CO3 / dimethylformamide / 50 °C
View Scheme
6-amino-1,3-diethyl-5-nitroso-1H,3H-pyrimidine-2,4-dione
89073-60-9

6-amino-1,3-diethyl-5-nitroso-1H,3H-pyrimidine-2,4-dione

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 80 percent / NH3; sodium dithionite / H2O / 60 °C
2: 65 percent / pyridine / CH2Cl2 / 16 h / 20 °C
3: 92 percent / 1,1,1,3,3,3-hyxamethyldisilazane; (NH4)2SO4 / 4 h / 170 - 180 °C
4: 95 percent / potassium carbonate / dimethylformamide / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: ammonium hydroxide; sodium dithionite / water / 0.5 h
2.1: pyridine / dichloromethane / 24 h / 20 °C
3.1: acetonitrile / Microwave irradiation
3.2: 5 h / 160 °C / Microwave irradiation
4.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: palladium 10% on activated carbon; hydrogen / methanol / 15 °C / 3750.38 - 4500.45 Torr
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 10 - 35 °C
3: sodium hydroxide / propan-1-ol / 5 h / Reflux
4: potassium carbonate / N,N-dimethyl-formamide / 3 h / 50 - 60 °C
5: acetic acid; acetic anhydride / 10 h / 110 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / water / 30 - 50 °C
1.2: 1 h / 20 °C
2.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1.5 h / 25 °C
2.2: 1 h / 20 °C
3.1: sodium hydroxide / water; 1,4-dioxane / 2 h / 60 °C
4.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Darkness
View Scheme
6-amino-1,3-diethyluracil
41740-15-2

6-amino-1,3-diethyluracil

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 74 percent / acetic acid; NaNO2 / H2O / 0.25 h / 50 - 60 °C
2: 80 percent / NH3; sodium dithionite / H2O / 60 °C
3: 65 percent / pyridine / CH2Cl2 / 16 h / 20 °C
4: 92 percent / 1,1,1,3,3,3-hyxamethyldisilazane; (NH4)2SO4 / 4 h / 170 - 180 °C
5: 95 percent / potassium carbonate / dimethylformamide / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: sodium nitrite / acetic acid / 0.25 h / 50 - 60 °C
2.1: ammonium hydroxide; sodium dithionite / water / 0.5 h
3.1: pyridine / dichloromethane / 24 h / 20 °C
4.1: acetonitrile / Microwave irradiation
4.2: 5 h / 160 °C / Microwave irradiation
5.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
(E)-N-(6-amino-1,3-diethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(3,4-dimethoxyphenyl)propenamide
187393-68-6

(E)-N-(6-amino-1,3-diethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(3,4-dimethoxyphenyl)propenamide

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / 1,1,1,3,3,3-hyxamethyldisilazane; (NH4)2SO4 / 4 h / 170 - 180 °C
2: 95 percent / potassium carbonate / dimethylformamide / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: acetonitrile / Microwave irradiation
1.2: 5 h / 160 °C / Microwave irradiation
2.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
3,4-dimethoxy-trans-cinnamic acid
14737-89-4

3,4-dimethoxy-trans-cinnamic acid

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: EDAC / dioxane; H2O
1.2: 35 percent / aq. NaOH / Heating
2.1: K2CO3 / dimethylformamide
View Scheme
Multi-step reaction with 2 steps
1: 1) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, 2) 1N NaOH / 1) dioxane, H2O, 2) dioxane, H2O, reflux
2: K2CO3 / dimethylformamide / 50 °C
View Scheme
Multi-step reaction with 4 steps
1.1: thionyl chloride / toluene / 16 h / 75 °C
2.1: pyridine / dichloromethane / 24 h / 20 °C
3.1: acetonitrile / Microwave irradiation
3.2: 5 h / 160 °C / Microwave irradiation
4.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
N,N-diethylurea
634-95-7

N,N-diethylurea

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: acetic acid / 2 h / 80 °C
2.1: sodium nitrite / acetic acid / 0.25 h / 50 - 60 °C
3.1: ammonium hydroxide; sodium dithionite / water / 0.5 h
4.1: pyridine / dichloromethane / 24 h / 20 °C
5.1: acetonitrile / Microwave irradiation
5.2: 5 h / 160 °C / Microwave irradiation
6.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
(E)-3,4-dimethoxycinnamic chloride
39856-08-1, 141236-46-6

(E)-3,4-dimethoxycinnamic chloride

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: pyridine / dichloromethane / 24 h / 20 °C
2.1: acetonitrile / Microwave irradiation
2.2: 5 h / 160 °C / Microwave irradiation
3.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: pyridine / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 20 °C / Large scale
2: sodium hydroxide / isopropyl alcohol; water / 75 - 80 °C
3: potassium carbonate / N,N-dimethyl-formamide / 10 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 5 h / 5 - 35 °C
2: N,N'-diethylurea / 1,4-dioxane / 4 h / 90 - 95 °C
View Scheme
5,6-diamino-1,3-diethylpyrimidine-2,4-(1H,3H)-dione hydrochloride

5,6-diamino-1,3-diethylpyrimidine-2,4-(1H,3H)-dione hydrochloride

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 10 - 35 °C
2: sodium hydroxide / propan-1-ol / 5 h / Reflux
3: potassium carbonate / N,N-dimethyl-formamide / 3 h / 50 - 60 °C
4: acetic acid; acetic anhydride / 10 h / 110 °C
View Scheme
N-(6-amino-1,3-diethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide

N-(6-amino-1,3-diethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / propan-1-ol / 5 h / Reflux
2: potassium carbonate / N,N-dimethyl-formamide / 3 h / 50 - 60 °C
3: acetic acid; acetic anhydride / 10 h / 110 °C
View Scheme
3,4-dimethoxystyrene
6380-23-0

3,4-dimethoxystyrene

1,3-diethyl-8-iodo-7-methylpurine-2,6-dione

1,3-diethyl-8-iodo-7-methylpurine-2,6-dione

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; palladium dichloride In N,N-dimethyl-formamide at 100℃; for 12h; Inert atmosphere;58.87 g
With N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; palladium dichloride In N,N-dimethyl-formamide at 100℃; for 12h; Inert atmosphere;58.87 g
N,N'-diethylurea
623-76-7

N,N'-diethylurea

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1,4-dioxane / 4 h / 100 - 105 °C
2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 4 h / 10 - 55 °C
3: sodium methylate / 1,4-dioxane / 3 h / 90 - 95 °C
View Scheme
5,6-diamino-1,3-diethyluracil
52998-22-8

5,6-diamino-1,3-diethyluracil

(E)-3,4-dimethoxycinnamic chloride
39856-08-1, 141236-46-6

(E)-3,4-dimethoxycinnamic chloride

istradefylline
155270-99-8

istradefylline

Conditions
ConditionsYield
With sodium carbonate In ethanol at 60℃; for 3.5h;
istradefylline
155270-99-8

istradefylline

(1α,2α,3β,4β)-1,3-bis[1,3-diethyl-7-methyl-3,7-dihydropurine-2,6-dion-8-yl]-2,4-bis(3,4-dimethoxyphenyl)cyclobutane

(1α,2α,3β,4β)-1,3-bis[1,3-diethyl-7-methyl-3,7-dihydropurine-2,6-dion-8-yl]-2,4-bis(3,4-dimethoxyphenyl)cyclobutane

Conditions
ConditionsYield
With aluminum (III) chloride In chloroform at 30 - 40℃; for 10h; UV-irradiation; Inert atmosphere;87.2%
for 1.66667h; Irradiation;12 mg
1,5-dibromo-pentane
111-24-0

1,5-dibromo-pentane

istradefylline
155270-99-8

istradefylline

(E)-7,7'-(pentane-1,5-diyl)bis(8-((E)-3,4-dimethoxystyryl)-1,3-diethyl-1H-purine-2,6(3H,7H)-dione)

(E)-7,7'-(pentane-1,5-diyl)bis(8-((E)-3,4-dimethoxystyryl)-1,3-diethyl-1H-purine-2,6(3H,7H)-dione)

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In acetone at 20℃;69.2%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

istradefylline
155270-99-8

istradefylline

(E)-7-(5-bromobutyl)-8-(3,4-dimethoxystyryl)-1,3-diethyl-1H-purine-2,6( 3H,7H)-dione

(E)-7-(5-bromobutyl)-8-(3,4-dimethoxystyryl)-1,3-diethyl-1H-purine-2,6( 3H,7H)-dione

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In acetone at 20℃;59.9%
istradefylline
155270-99-8

istradefylline

(Z)-1,3-diethyl-8-(3,4-dimethoxystyryl)-7-methylxanthine

(Z)-1,3-diethyl-8-(3,4-dimethoxystyryl)-7-methylxanthine

Conditions
ConditionsYield
In acetone Irradiation;16%

Istradefylline Specification

The Istradefylline, with the CAS registry number 155270-99-8, is also known as (E)-8-(3,4-Dimethoxystyryl)-1,3-diethyl-7-methylxanthine. This chemical's molecular formula is C20H24N4O4 and molecular weight is 384.43. What's more, its systematic name is 8-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-7-methylpurine-2,6-dione. Its classification codes are: (1)Antiparkinsonian; (2)Drug / Therapeutic Agent; (3)Treatment of Parkinson's disease [adenosine A2A receptor antagonist]. It has been found to be useful in the treatment of Parkinson's disease. It reduces dyskinesia resulting from long-term treatment with classical antiparkinson drugs such as levodopa.

Physical properties of Istradefylline are: (1)ACD/LogP: 2.84; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.84; (4)ACD/LogD (pH 7.4): 2.84; (5)ACD/BCF (pH 5.5): 84.87; (6)ACD/BCF (pH 7.4): 84.87; (7)ACD/KOC (pH 5.5): 835.99; (8)ACD/KOC (pH 7.4): 836.01; (9)#H bond acceptors: 8; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 76.9 Å2; (13)Index of Refraction: 1.598; (14)Molar Refractivity: 105.55 cm3; (15)Molar Volume: 309.1 cm3; (16)Polarizability: 41.84×10-24cm3; (17)Surface Tension: 44 dyne/cm; (18)Density: 1.24 g/cm3; (19)Flash Point: 317.3 °C; (20)Enthalpy of Vaporization: 89.44 kJ/mol; (21)Boiling Point: 601 °C at 760 mmHg; (22)Vapour Pressure: 2.12E-14 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCN1C2=C(C(=O)N(C1=O)CC)N(C(=N2)C=CC3=CC(=C(C=C3)OC)OC)C
(2)Isomeric SMILES: CCN1C2=C(C(=O)N(C1=O)CC)N(C(=N2)/C=C/C3=CC(=C(C=C3)OC)OC)C
(3)InChI: InChI=1S/C20H24N4O4/c1-6-23-18-17(19(25)24(7-2)20(23)26)22(3)16(21-18)11-9-13-8-10-14(27-4)15(12-13)28-5/h8-12H,6-7H2,1-5H3/b11-9+
(4)InChIKey: IQVRBWUUXZMOPW-PKNBQFBNSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD oral > 300mg/kg (300mg/kg)   United States Patent Document. Vol. #5543415,

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