9-(Tetrahydrofuran-2-yl)-9h-purin-6-amine

Base Information

• Chemical Name: 9-(Tetrahydrofuran-2-yl)-9h-purin-6-amine
• CAS No.: 17318-31-9
• Molecular Formula: C₉H₁₁N₅O
• Molecular Weight: 205.219
• Hs Code.: 2934999090
• European Community (EC) Number: 633-987-7
• NSC Number: 53339
• Nikkaji Number: J336.544A
• Wikidata: Q27162414
• ChEMBL ID: CHEMBL64239
• Mol file: 17318-31-9.mol

Synonyms:9-(tetrahydro-2-furyl)-adenine;Sq 22,536;SQ 22536;SQ-22,536;SQ-22536

Chemical Property of 9-(Tetrahydrofuran-2-yl)-9h-purin-6-amine

Chemical Property:

• Appearance/Colour: White to off-white solid
• Vapor Pressure: 3.49E-09mmHg at 25°C
• Melting Point: 160-161 °C
• Refractive Index: 1.83
• Boiling Point: 474.8 °C at 760 mmHg
• PKA: 3.82±0.10(Predicted)
• Flash Point: 241 °C
• PSA: 78.85000
• Density: 1.7 g/cm³
• LogP: 1.29870
• Storage Temp.: 0-6°C
• Solubility.: H2O: 21 mg/mL
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 205.09635999
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

98%,99%, ^*data from raw suppliers

SQ 22536 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(OC1)N2C=NC3=C(N=CN=C32)N
• Description: SQ 22,536 is an inhibitor of adenylyl cyclase with an IC50 value of 13 μM for inhibition of prostaglandin E1-stimulated increase in cAMP in intact platelets. It has been used to evaluate adenylyl cyclase activity during iloprost-induced vasorelaxation of isolated pulmonary veins or aorta in several research paradigms, inhibiting cAMP elevation at concentrations of 100-300 μM without effecting relaxation.
• Uses: SQ 22,536 was used to study the role of adenylate cyclase in differentiation of PC12 cells and in gap junctional intercellular communication in breast cancer cells.

Technology Process of 9-(Tetrahydrofuran-2-yl)-9h-purin-6-amine

There total 8 articles about 9-(Tetrahydrofuran-2-yl)-9h-purin-6-amine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(+/-)-N9-(1-Oxa-3-cyclopenten-2-yl)adenine (114987-20-1) → 9-(tetrahydro-2-furanyl)-9H-purine-6-amine (17318-31-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 15h; under 2585.7 Torr;

DOI:10.1021/ja00197a063

Reference yield: 90.0%

tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → 9-(tetrahydro-2-furanyl)-9H-purine-6-amine (17318-31-9)

Guidance literature:

With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; at 90 ℃; for 12h; Sealed tube;

Reference yield: 28.0%

2,3-dihydro-2H-furan (1191-99-7,75454-45-4) + adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → 9-(tetrahydro-2-furanyl)-9H-purine-6-amine (17318-31-9)

Guidance literature:

With ethanesulfuric acid; In ethyl acetate; at 50 ℃;

DOI:10.1021/jm00113a029

upstream raw materials:

2,3-dihydro-2H-furan

adenine

2-acetoxytetrahydrofuran

(+/-)-N⁹-(1-Oxa-3-cyclopenten-2-yl)adenine

Refernces

• 1、 Luo, Zheng,Jiang, Ziyang,Jiang, Wei,Lin, Dongen. "C-H amination of purine derivatives via radical oxidative coupling". . p. 3710 - 3718. Retrieved 2018/04/14.
• 2、 Lee, Chun Ho,Kim, Joong Young,Kim, Wan Joo,Kim, Yong Hae. "FACILE SYNTHESIS OF TETRAHYDRO-2-FURYLATED PYRIMIDINES AND PURINES USING A NEW CATALYST OF CESIUM CHLORIDE". . p. 211 - 214. Retrieved 2007/10/02.