35206-02-1

Basic information

• Product Name: 7-(2-aminoethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione
• Synonyms: 7-(2-aminoethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione;7-(2-Aminoethyl)theophylline;1H-Purine-2,6-dione, 7-(2-aminoethyl)-3,7-dihydro-1,3-dimethyl- (9ci);Aminoaethyl theophyllin;Aminoaethyl theophyllin [german];Aminoethyl theophylline;Brn 0251762;Einecs 252-436-8
• CAS NO: 35206-02-1
• Molecular Formula: C₉H₁₃N₅O₂
• Molecular Weight: 223.23182
• EINECS: 252-436-8
• Mol File: 35206-02-1.mol

Chemical Properties

• Melting Point: 187-190 °C
• Boiling Point: 470.7°Cat760mmHg
• Flash Point: 238.5°C
• Appearance: /
• Density: 1.51g/cm³
• Vapor Pressure: 4.96E-09mmHg at 25°C
• Refractive Index: 1.703
• PKA: 9.02±0.10(Predicted)
• CAS DataBase Reference: 7-(2-aminoethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 7-(2-aminoethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione(35206-02-1)
• EPA Substance Registry System: 7-(2-aminoethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione(35206-02-1)

Safety Data

• Hazardous Substances Data: 35206-02-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
7-(2-aminoethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione is used as a research compound for its potential biological activities, including its antioxidant and anti-inflammatory properties. Its structural resemblance to caffeine also makes it a candidate for studying effects on the central nervous system.
Used in Antioxidant Applications:
7-(2-aminoethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione is used as an antioxidant agent, potentially protecting cells from oxidative stress and damage caused by reactive oxygen species.
Used in Anti-inflammatory Applications:
7-(2-aminoethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione is used as an anti-inflammatory agent, potentially reducing inflammation and alleviating symptoms associated with inflammatory conditions.
Used in Central Nervous System Applications:
7-(2-aminoethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione is used as a compound for studying its potential effects on the central nervous system, due to its structural resemblance to caffeine.
Used in Medicinal Chemistry:
7-(2-aminoethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione is used as a promising molecule in medicinal chemistry for the development of new drugs and therapeutic agents.
Used in Pharmacology:
7-(2-aminoethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione is used in pharmacological research to understand its pharmacological properties and potential applications in treating various diseases and conditions.

InChI:InChI=1/C9H13N5O2/c1-12-7-6(8(15)13(2)9(12)16)14(4-3-10)5-11-7/h5H,3-4,10H2,1-2H3

Synthetic route

ethyleneimine (151-56-4) + theophylline (58-55-9) → 7-(2-Aminoethyl)theophylline (35206-02-1)

Conditions	Yield
In 2-ethoxy-ethanol at 70℃;	62%

7-(2-chloroethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione (5878-61-5) → 7-(2-Aminoethyl)theophylline (35206-02-1)

Conditions	Yield
With ethanol; ammonia

1,3-dimethyl-7-(2-phthalimido-ethyl)-3,7-dihydro-purine-2,6-dione (70454-20-5) → 7-(2-Aminoethyl)theophylline (35206-02-1)

Conditions	Yield
With ethanol; hydrazine hydrate

7-(2-Aminoethyl)theophylline (35206-02-1) + N,N-Dimethyl-N'-(2,6-dichlorophenyl)-C-chloroformamidine hydrochloride (66156-58-9) → N,N-Dimethyl-N'-<β-(7-theophyllinyl)ethyl>-N''-(2,6-dichlorophenyl)guanidine (85461-01-4)

Conditions	Yield
With triethylamine In acetonitrile at 20 - 22℃; for 16h;	79%

3,6-dichlorpyridazine (141-30-0) + 7-(2-Aminoethyl)theophylline (35206-02-1) → 3-chloro-<6-<2-(7-theophyllin)-ethyl>-amino>-pyridazine

Conditions	Yield
In i-Amyl alcohol Heating;	50%

7-(2-Aminoethyl)theophylline (35206-02-1) + S-Methylisothiourea sulfate (867-44-7) → 7-(β-Guanidinoethyl)theophyllin hemisulfate (63077-40-7)

Conditions	Yield
In ethanol for 4h; Heating;	37.1%

4,5-dichloro-2H-pyridazin-3-one (932-22-9) + 7-(2-Aminoethyl)theophylline (35206-02-1) → 4-<<2-(7-theophyllin)-ethyl>-amino>-5-chloro-3(2H)-pyridazinone + 4-chloro-5-<<2-(7-theophyllin)-ethyl>-amino>-3(2H)-pyridazinone

Conditions	Yield
With potassium hydrogencarbonate In 1,4-dioxane at 80℃; for 10h;	A 20% B 15%

4,5-dichloro-2-methyl-3(2H)-pyridazinone (933-76-6) + 7-(2-Aminoethyl)theophylline (35206-02-1) → 2-methyl-4-<<2-(7-theophyllin)-ethyl>-amino>-5-chloro-3(2H)-pyridazinone + 2-methyl-4-chloro-5-<<2-(7-theophyllin)-ethyl>-amino>-3(2H)-pyridazinone

Conditions	Yield
With potassium hydrogencarbonate In 1,4-dioxane for 30h; Heating;	A 20% B 10%

4-oxo-4H-chromene-2-carboxylic acid butyl ester (51081-67-5) + 7-(2-Aminoethyl)theophylline (35206-02-1) → 4-oxo-4H-chromene-2-carboxylic acid 2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-ethylamide (109694-00-0)

Conditions	Yield
With methanol Erwaermen des Reaktionsprodukts mit Essigsaeure und konz.wss.HCl;

7-(2-Aminoethyl)theophylline (35206-02-1) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → N-acetyl-sulfanilic acid-[2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-ethylamide] (857547-76-3)

Conditions	Yield
With sodium hydrogencarbonate; acetone

3-Benzoylpyridine (5424-19-1) + 7-(2-Aminoethyl)theophylline (35206-02-1) → 1,3-Dimethyl-7-{2-[(phenyl-pyridin-3-yl-methyl)-amino]-ethyl}-3,7-dihydro-purine-2,6-dione; hydrochloride

Conditions	Yield
With hydrogenchloride; sodium tetrahydroborate 1.) 120-130 deg C, 5 h; 2.) methanol; Yield given. Multistep reaction;

4-(4-chlorobenzoyl)pyridine (14548-48-2) + 7-(2-Aminoethyl)theophylline (35206-02-1) → 7-(2-{[(4-Chloro-phenyl)-pyridin-4-yl-methyl]-amino}-ethyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione; hydrochloride

Conditions	Yield
With hydrogenchloride; sodium tetrahydroborate 1.) 120-130 deg C, 5 h; 2.) methanol; Yield given. Multistep reaction;

3-chlorobenzophenone (1016-78-0) + 7-(2-Aminoethyl)theophylline (35206-02-1) → 7-[2-(3-chloro-benzhydrylamino)-ethyl]-1,3-dimethyl-3,7-dihydro-purine-2,6-dione (72754-68-8)

Conditions	Yield
With sodium tetrahydroborate 1.) 120-130 deg C, 5 h; 2.) methanol; Yield given. Multistep reaction;

7-(2-Aminoethyl)theophylline (35206-02-1) + dichloromethylenedimethyliminium chloride (33842-02-3, 529510-96-1) → C12H17ClN6O2 (85460-96-4)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 16h;

7-(2-Aminoethyl)theophylline (35206-02-1) + 4-chlorobenzophenone (134-85-0) → 7-(2-{[(4-Chloro-phenyl)-phenyl-methyl]-amino}-ethyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione

Conditions	Yield
With sodium tetrahydroborate 1.) 120-130 deg C, 5 h; 2.) methanol; Yield given. Multistep reaction;

7-(2-Aminoethyl)theophylline (35206-02-1) → 6-<<2-(7-theophyllin)-ethyl>-amino>-3(2H)-pyridazinone

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / 3-methyl-butan-1-ol / Heating 2: 25 percent / glacial CH3COOH / 14 h / Heating View Scheme

7-(2-Aminoethyl)theophylline (35206-02-1) → N,N-Dimethyl-N'-<β-(7-theophyllinyl)ethyl>urea (85460-97-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 16 h / 20 °C 2: H2O, NaHCO3 / 16 h / 20 °C View Scheme

7-(2-Aminoethyl)theophylline (35206-02-1) → 1,2-Bis- (85461-00-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N / CH2Cl2 / 16 h / 20 °C 2: 22.7 percent / acetonitrile / 20 °C 3: 63 percent / H2O / 3.5 h / Heating View Scheme

7-(2-Aminoethyl)theophylline (35206-02-1) → N'-[2-(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-ethyl]-N''-(2-{N''-[2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-ethyl]-N',N'-dimethyl-guanidino}-ethyl)-N,N-dimethyl-guanidine (85460-99-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 16 h / 20 °C 2: 22.7 percent / acetonitrile / 20 °C View Scheme

7-(2-Aminoethyl)theophylline (35206-02-1) → N,N-Dimethyl-N'-<β-(7-theophyllinyl)ethyl>guanidine

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 16 h / 20 °C 2: NH3 / acetonitrile / 20 °C View Scheme

7-(2-Aminoethyl)theophylline (35206-02-1) → sulfanilic acid-[2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-ethylamide]

Conditions	Yield
Multi-step reaction with 2 steps 1: NaHCO3; aqueous acetone 2: aq.-ethanolic HCl View Scheme

Upstream product

• 70454-20-5 1,3-dimethyl-7-(2-phthalimido-ethyl)-3,7-dihydro-purine-2,6-dione 
• 151-56-4 ethyleneimine 
• 58-55-9 theophylline 
• 5878-61-5 7-(2-chloroethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione 

Downstream Products

• 857547-76-3 N-acetyl-sulfanilic acid-[2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-ethylamide] 
• 85461-01-4 N,N-Dimethyl-N'-<β-(7-theophyllinyl)ethyl>-N''-(2,6-dichlorophenyl)guanidine 
• 63077-40-7 7-(β-Guanidinoethyl)theophyllin hemisulfate 
• 72754-68-8 7-[2-(3-chloro-benzhydrylamino)-ethyl]-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 
• 85460-97-5 N,N-Dimethyl-N'-<β-(7-theophyllinyl)ethyl>urea 

Relevant articles and documents

Nucleophilic ring opening of aziridines

This account of research work on nucleophilic ring opening (NRO) of aziridines (Az's) demonstrates the broad synthetic scope of this reaction, inclusive secondary reactions, and it discusses the special mechanistic fundamentals and details as well as mechanistic variants. Formation of a C-C bond by NRO is the red thread in this report. A central mechanistic aspect is the quality of the leaving group in Az bases, aziridinium ions and activated Az's (acyl, sulfonyl; double activation). Factors controlling the regioselectivity of NRO are dealt with as well as the influence of the nitrogen pyramid. Competing reactions include carbonyl attack (acylated Az's) and electron transfer with cases of pseudo-NRO (multistep radical paths). Wiley-VCH Verlag GmbH, 1999.