N6-Cyclopropyl-9H-purine-2,6-diamine

Base Information

• Chemical Name: N6-Cyclopropyl-9H-purine-2,6-diamine
• CAS No.: 120503-69-7
• Molecular Formula: C8H10 N6
• Molecular Weight: 190.208
• Hs Code.: 2933990090
• UNII: Y5E53WSA7U
• DSSTox Substance ID: DTXSID80431151
• Wikidata: Q27294284
• ChEMBL ID: CHEMBL4170763
• Mol file: 120503-69-7.mol

Synonyms:N6-Cyclopropyl-9H-purine-2,6-diamine;120503-69-7;2-Amino-6-cyclopropylaminopurine;2-amino-6-cyclopropylamino-9h-purine;6-N-cyclopropyl-7H-purine-2,6-diamine;Y5E53WSA7U;Cyclopropyldiaminopurine abacavir;N6-Cyclopropyl-9H-purine-2,6-diamine Methanolate;2-Amino-6-(cyclopropylamino)-9H-purine;1H-Purine-2,6-diamine, N6-cyclopropyl-;9H-Purine-2,6-diamine, N6-cyclopropyl-;UNII-Y5E53WSA7U;SCHEMBL133156;CHEMBL4170763;DTXSID80431151;IYWUSKBMXQERLH-UHFFFAOYSA-N;STK659364;AKOS005590032;AKOS016012903;DS-5343;N~6~-cyclopropyl-7H-purine-2,6-diamine;Abacavir Cyclopropyl Diamino Purine Impurity;CS-0187573;C71699;A906969;Q27294284

Chemical Property of N6-Cyclopropyl-9H-purine-2,6-diamine

Chemical Property:

• Melting Point: 172-174oC
• PSA: 96.47000
• Density: 1.97
• LogP: -0.13860
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 190.09669434
• Heavy Atom Count: 14
• Complexity: 218

Purity/Quality:

99% ^*data from raw suppliers

N6-Cyclopropyl-9H-purine-2,6-diamineMethanolate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1NC2=NC(=NC3=C2NC=N3)N
• Uses: N6-Cyclopropyl-9H-purine-2,6-diamine is an impurity of Abacavir Sulfate (A105000), a nucleoside reverse transcriptase inhibitor. N6-Cyclopropyl-9H-purine-2,6-diamine is an impurity of Abacavir Sulfate (A105000), a nucleoside reverse transcriptase inhibitor (1,2,3). 2-Amino-6-cyclopropylamino-9H-purine is used in preparation of Purine derivatives as AMPK activating compounds.

Technology Process of N6-Cyclopropyl-9H-purine-2,6-diamine

There total 2 articles about N6-Cyclopropyl-9H-purine-2,6-diamine 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: 87.6%

2-Amino-6-chloropurin (10310-21-1) + Cyclopropylamine (765-30-0) → 2-amino-6-(cyclopropylamino)purine (120503-69-7)

Guidance literature:

In ethanol; for 8h; Heating;

DOI:10.1135/cccc20011545

Reference yield:

→ 2-amino-6-(cyclopropylamino)purine (120503-69-7)

Guidance literature:

With triethylamine; In butan-1-ol; at 90 ℃; for 4h;

Reference yield:

2-amino-6-(cyclopropylamino)purine (120503-69-7) → abacavir (136470-78-5,128131-83-9,136470-79-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / NaH; Pd(PPh₃)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C

2: aq. NaOH

With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1021/jo005535p

upstream raw materials:

2-Amino-6-chloropurin

Cyclopropylamine

Downstream raw materials:

(S)-1-(2-Amino-6-cyclopropylamino-purin-9-yl)-3-trityloxy-propan-2-ol

abacavir

Refernces

• 1、 Holy, Antonin,Votruba, Ivan,Tloustova, Eva,Masojidkova, Milena. "Synthesis and cytostatic activity of N-[2-(phosphonomethoxy)alkyl] derivatives of N6-substituted adenines, 2,6-diaminopurines and related compounds". . p. 1545 - 1592. Retrieved 2007/10/03.