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Basic Information

Molecular Structure:
CAS No.:	58-32-2
Name:	Dipyridamole
Article Data:	17
Cas Database

Formula:	C₂₄H₄₀N₈O₄
Molecular Weight:	504.633
Synonyms:	Ethanol,2,2',2'',2'''-[(4,8-dipiperidinopyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetra-(6CI,8CI);2,2',2'',2'''-[[4,8-Dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyl]dinitrilo]tetraethanol;2,6-Bis(diethanolamino)-4,8-dipiperidinopyrimido[5,4-d]pyrimidine;Anginal;Apricor;Cardioflux;Cardoxil;Cardoxin;Cleridium;Coronarine;Corosan;Coroxin;Curantyl;Gulliostin;Kurantil;Peridamol;Persantin;Persantine;Piroan;Prandiol;
EINECS:	200-374-7
Density:	1.352 g/cm³
Melting Point:	165-166 °C(lit.)
Boiling Point:	806.5 °C at 760 mmHg
Flash Point:	441.5 °C
Solubility:	soluble in DMSO
Appearance:	Yellow Powder
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36
PSA:	145.44000
LogP:	0.11240

Synthetic route

: 7139-02-8
2,6-dichloro-4,8-bis(piperidin-1-yl)pyrimido[5,4-d]pyrimidine

: 111-42-2
2,2'-iminobis[ethanol]

: 58-32-2
dipyridamole

Conditions

Conditions	Yield
Stage #1: 2,6-dichloro-4,8-bis(piperidin-1-yl)pyrimido[5,4-d]pyrimidine; 2,2'-iminobis[ethanol] In toluene at 0 - 155℃; for 9.5h; Stage #2: With benzenesulfonic acid In water; toluene at 0 - 95℃; for 2h; Stage #3: With ammonia; pyrographite In ethanol for 0.333333h; pH=8; Temperature;	95%
With 001x7 strong acid cation exchange resin In 1,3-dioxane at 78℃; for 4.5h; Temperature;	75%
Stage #1: 2,6-dichloro-4,8-bis(piperidin-1-yl)pyrimido[5,4-d]pyrimidine; 2,2'-iminobis[ethanol] at 180℃; for 3h; Stage #2: With sodium hydroxide In water; acetone at 25℃; for 4h;	70%

: C16H24N6O2

: 111-42-2
2,2'-iminobis[ethanol]

: 58-32-2
dipyridamole

Conditions

Conditions	Yield
With hydrogen at 240℃; under 11251.1 Torr; for 3h;	50.31%

: 110-89-4
piperidine

2-<2,6-dihydroxy-3,5-dimethyl-phenoxy>-3,5-dinitro-benzophenone: 2-<2,6-dihydroxy-3,5-dimethyl-phenoxy>-3,5-dinitro-benzophenone

: 58-32-2
dipyridamole

Conditions

Conditions	Yield
1: Substitution / 2: Substitution;

: 32980-71-5
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine

: 58-32-2
dipyridamole

Conditions

Conditions	Yield
1: Substitution / 2: Substitution;
Multi-step reaction with 2 steps 1: acetone; tetrachloromethane / 1 h / 30 °C 2: 0.25 h / 200 °C View Scheme

: 54093-92-4
2,2'-(6-chloro-4,8-di-piperidin-1-yl-pyrimido[5,4-d]pyrimidin-2-ylazanediyl)-bis-ethanol

: 111-42-2
2,2'-iminobis[ethanol]

: 58-32-2
dipyridamole

Conditions

Conditions	Yield
at 25 - 115℃;

: 6713-54-8
2,4,6,8-tetrahydroxypyrimidine-[5,4-d]pyrimidine

: 58-32-2
dipyridamole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1,4-dioxane / 1 h 1.2: 1.5 h / Darkness 2.1: caesium carbonate; copper(l) iodide / nitrobenzene / 16 h / 180 °C / Inert atmosphere 3.1: 3 h / 180 °C 3.2: 4 h / 25 °C View Scheme
Multi-step reaction with 3 steps 1: trichlorophosphate; phosphorus trichloride; chlorine / 24 h / 110 °C 2: acetone; tetrachloromethane / 1 h / 30 °C 3: 0.25 h / 200 °C View Scheme

: 626-48-2
6-Methyluracil

: 58-32-2
dipyridamole

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: 2,2'-azobis(isobutyronitrile); cobalt(II) acetate; acetic acid; oxygen / 15 h / 80 °C 2.1: sodium hydroxide / water / 3 h 2.2: 25 - 45 °C / Inert atmosphere 3.1: copper; hydrogenchloride / water / 13 h / 40 °C / Inert atmosphere 4.1: sodium hydroxide / water / 4 h / 100 °C 5.1: thionyl chloride / 1,4-dioxane / 1 h 5.2: 1.5 h / Darkness 6.1: caesium carbonate; copper(l) iodide / nitrobenzene / 16 h / 180 °C / Inert atmosphere 7.1: 3 h / 180 °C 7.2: 4 h / 25 °C View Scheme
Multi-step reaction with 7 steps 1.1: sodium hydroxide; water; oxygen / 95 °C 2.1: nitric acid; sulfuric acid / 1 h / 10 - 30 °C 3.1: sodium dithionite / water / 0.5 h / 35 °C 4.1: 0.33 h / 100 °C 4.2: 1 h / 90 - 100 °C 4.3: 0.5 h / 60 °C / pH 4 5.1: trichlorophosphate; phosphorus trichloride; chlorine / 24 h / 110 °C 6.1: acetone; tetrachloromethane / 1 h / 30 °C 7.1: 0.25 h / 200 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: 2,2'-azobis(isobutyronitrile); cobalt(II) acetate; acetic acid; oxygen / 15 h / 80 °C
2.1: sodium hydroxide / water / 3 h
2.2: 25 - 45 °C / Inert atmosphere
3.1: copper; hydrogenchloride / water / 13 h / 40 °C / Inert atmosphere
4.1: sodium hydroxide / water / 4 h / 100 °C
5.1: thionyl chloride / 1,4-dioxane / 1 h
5.2: 1.5 h / Darkness
6.1: caesium carbonate; copper(l) iodide / nitrobenzene / 16 h / 180 °C / Inert atmosphere
7.1: 3 h / 180 °C
7.2: 4 h / 25 °C
View Scheme

Multi-step reaction with 7 steps
1.1: sodium hydroxide; water; oxygen / 95 °C
2.1: nitric acid; sulfuric acid / 1 h / 10 - 30 °C
3.1: sodium dithionite / water / 0.5 h / 35 °C
4.1: 0.33 h / 100 °C
4.2: 1 h / 90 - 100 °C
4.3: 0.5 h / 60 °C / pH 4
5.1: trichlorophosphate; phosphorus trichloride; chlorine / 24 h / 110 °C
6.1: acetone; tetrachloromethane / 1 h / 30 °C
7.1: 0.25 h / 200 °C
View Scheme

: 65-86-1
orotic acid

: 58-32-2
dipyridamole

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: sodium hydroxide / water / 3 h 1.2: 25 - 45 °C / Inert atmosphere 2.1: copper; hydrogenchloride / water / 13 h / 40 °C / Inert atmosphere 3.1: sodium hydroxide / water / 4 h / 100 °C 4.1: thionyl chloride / 1,4-dioxane / 1 h 4.2: 1.5 h / Darkness 5.1: caesium carbonate; copper(l) iodide / nitrobenzene / 16 h / 180 °C / Inert atmosphere 6.1: 3 h / 180 °C 6.2: 4 h / 25 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: sodium hydroxide / water / 3 h
1.2: 25 - 45 °C / Inert atmosphere
2.1: copper; hydrogenchloride / water / 13 h / 40 °C / Inert atmosphere
3.1: sodium hydroxide / water / 4 h / 100 °C
4.1: thionyl chloride / 1,4-dioxane / 1 h
4.2: 1.5 h / Darkness
5.1: caesium carbonate; copper(l) iodide / nitrobenzene / 16 h / 180 °C / Inert atmosphere
6.1: 3 h / 180 °C
6.2: 4 h / 25 °C
View Scheme

: 17687-24-0
5-nitroorotic acid

: 58-32-2
dipyridamole

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: copper; hydrogenchloride / water / 13 h / 40 °C / Inert atmosphere 2.1: sodium hydroxide / water / 4 h / 100 °C 3.1: thionyl chloride / 1,4-dioxane / 1 h 3.2: 1.5 h / Darkness 4.1: caesium carbonate; copper(l) iodide / nitrobenzene / 16 h / 180 °C / Inert atmosphere 5.1: 3 h / 180 °C 5.2: 4 h / 25 °C View Scheme
Multi-step reaction with 5 steps 1.1: sodium dithionite / water / 0.5 h / 35 °C 2.1: 0.33 h / 100 °C 2.2: 1 h / 90 - 100 °C 2.3: 0.5 h / 60 °C / pH 4 3.1: trichlorophosphate; phosphorus trichloride; chlorine / 24 h / 110 °C 4.1: acetone; tetrachloromethane / 1 h / 30 °C 5.1: 0.25 h / 200 °C View Scheme

: 7164-43-4
5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

: 58-32-2
dipyridamole

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide / water / 4 h / 100 °C 2.1: thionyl chloride / 1,4-dioxane / 1 h 2.2: 1.5 h / Darkness 3.1: caesium carbonate; copper(l) iodide / nitrobenzene / 16 h / 180 °C / Inert atmosphere 4.1: 3 h / 180 °C 4.2: 4 h / 25 °C View Scheme
Multi-step reaction with 4 steps 1.1: 0.33 h / 100 °C 1.2: 1 h / 90 - 100 °C 1.3: 0.5 h / 60 °C / pH 4 2.1: trichlorophosphate; phosphorus trichloride; chlorine / 24 h / 110 °C 3.1: acetone; tetrachloromethane / 1 h / 30 °C 4.1: 0.25 h / 200 °C View Scheme

Raw Materials

32980-71-5

54093-92-4

111-42-2

110-89-4

7139-02-8

Total:199 Page 1 of 6 1 2 3 4 5 6 Next>>

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Chemistry

Molecular Structure of Dypyridamole (CAS NO.58-32-2):

IUPAC Name: 2-[[2-[bis(2-hydroxyethyl)amino]-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol
Molecular Formula: C₂₄H₄₀N₈O₄
Molecular Weight: 504.63
EINECS: 200-374-7
H bond acceptors: 12
H bond donors: 4
Freely Rotating Bonds: 16
Polar Surface Area: 101.44Å²
Index of Refraction: 1.67
Molar Refractivity: 139.39 cm³
Molar Volume: 373 cm³
Surface Tension: 81.5 dyne/cm
Density: 1.352 g/cm³
Flash Point: 441.5 °C
Enthalpy of Vaporization: 122.94 kJ/mol
Boiling Point: 806.5 °C at 760 mmHg
Vapour Pressure: 1.82E-27 mmHg at 25°C
Melting point: 165-166 °C(lit.)
Storage temp: -20°C
Solubility: DMSO: soluble
Merck: 3346
InChI
InChI=1/C24H40N8O4/c33-15-11-31(12-16-34)23-26-20-19(21(27-23)29-7-3-1-4-8-29)25-24(32(13-17-35)14-18-36)28-22(20)30-9-5-2-6-10-30/h33-36H,1-18H2
Smiles
c12c(c(N3CCCCC3)nc(n2)N(CCO)CCO)nc(N(CCO)CCO)nc1N1CCCCC1
Product Categories: Organics; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Phosphodiesterase Inhibitors; Cyclic Nucleotide Metabolism; G Proteins and Cyclic Nucleotides; Cyclic Nucleotide related

Toxicity Data With Reference

1.	dni-rat:lvr 200 nmol/L	CNREA8 Cancer Research. 43 (1983),1616.
2.	oms-rat:lvr 300 nmol/L	CNREA8 Cancer Research. 43 (1983),1616.
3.	oms-mus:ast 60 µmol/L	BCPCA6 Biochemical Pharmacology. 22 (1973),2511.
4.	orl-man LDLo:1429 µg/kg:CVS	JAMAAP JAMA, Journal of the American Medical Association. 257 (1987),1515.
5.	orl-man TDLo:1071 µg/kg:CVS	JAMAAP JAMA, Journal of the American Medical Association. 257 (1987),1515.
6.	orl-rat LD₅₀:8400 mg/kg	MEIEDD Merck Index. 10 (1983),489.
7.	scu-rat LD₅₀:1650 mg/kg	ARZNAD Arzneimittel-Forschung. Drug Research. 22 (1972),892.
8.	ivn-rat LD₅₀:195 mg/kg	ARZNAD Arzneimittel-Forschung. Drug Research. 22 (1972),892.
9.	orl-mus LD₅₀:2150 mg/kg	ARZNAD Arzneimittel-Forschung. Drug Research. 11 (1961),848.
10.	ipr-mus LD₅₀:150 mg/kg	NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD691-490 .

Safety Profile

Poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion and subcutaneous routes. Human systemic effects cardiomyopathy including infarction. Mutation data reported. Used as a coronary vasodilator. When heated to decomposition it emits toxic fumes of NO_x.
Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 2

Specification

Dypyridamole , with CAS number of 58-32-2, can be called Ethanol,2,2',2'',2'''-[(4,8-dipiperidinopyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetra-(6CI,8CI) ; Pyrimido[5,4-d]pyrimidine, ethanol deriv ; 2,2',2'',2'''-[[4,8-Dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyl]dinitrilo]tetraethanol ; 2,6-Bis(diethanolamino)-4,8-dipiperidinopyrimido[5,4-d]pyrimidine . It is a yellow powder. Dypyridamole (CAS NO.58-32-2) is commonly used as anti-platelet aggregation drugs,coronary expansion drug for the prevention of recurrent myocardial infarction and angina pectoris, etc.