(E)-9-(prop-1-en-1-yl)-9H-purin-6-amine

Base Information

• Chemical Name: (E)-9-(prop-1-en-1-yl)-9H-purin-6-amine
• CAS No.: 1446486-33-4
• Molecular Formula: C₈H₉N₅
• Molecular Weight: 175.193
• Hs Code.: 2933599550
• Mol file: 1446486-33-4.mol

Synonyms:

Chemical Property of (E)-9-(prop-1-en-1-yl)-9H-purin-6-amine

Chemical Property:

• Boiling Point: 415.6±48.0 °C(Predicted)
• PKA: 4.08±0.10(Predicted)
• Density: 1.39±0.1 g/cm3(Predicted)

Purity/Quality:

NLT 98% ^*data from raw suppliers

MutagenicImpurityofTenofovirDisoproxil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (E)-9-(Prop-1-en-1-yl)-9H-purin-6-amine is a mutagenic impurity in tenofovir disoproxil fumarate and can potentially serve as a key blocking group for the synthesis of 1-?substituted adenines.

Technology Process of (E)-9-(prop-1-en-1-yl)-9H-purin-6-amine

There total 24 articles about (E)-9-(prop-1-en-1-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: 92.0%

9-allyl-9H-adenine (4121-39-5) → (E)-6-amino-9-(prop-1-en-1-yl)-9H-purine (1446486-33-4,1464851-21-5)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; at 100 ℃; for 0.333333h; stereoselective reaction;

DOI:10.1002/ejoc.201201455

Reference yield: 5.0%

1-(adenin-9-yl)propan-2-yl methanesulfonate (1446486-34-5) → (E)-6-amino-9-(prop-1-en-1-yl)-9H-purine (1446486-33-4,1464851-21-5) + 9-allyl-9H-adenine (4121-39-5)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; at 25 - 30 ℃; for 3h;

DOI:10.1080/00304948.2013.798576

Reference yield:

6-chloropurine (87-42-3) → (E)-6-amino-9-(prop-1-en-1-yl)-9H-purine (1446486-33-4,1464851-21-5)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium carbonate / N,N-dimethyl-formamide / 17 h / 20 °C / Inert atmosphere

2: ammonia / tert-butyl alcohol / 21 h / 120 °C

3: potassium carbonate / 7 h / 200 °C / Microwave irradiation

4: allyl halide / Alkaline conditions

5: potassium tert-butylate / dimethyl sulfoxide / 0.33 h / 100 °C

With potassium tert-butylate; ammonia; potassium carbonate; In dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1002/ejoc.201201455

upstream raw materials:

9-allyl-9H-adenine

adenine

6-chloropurine

6-chloro-7-(3-methylbut-2-en-1-yl)-7H-purine

Refernces

• 1、 Chavakula, Ramadas,Mutyala, Narayanarao,Chennupati, Srinivasarao. "Synthesis of (E)-9-(Propen-1-yl)-9 H-adenine, a mutagenic impurity in tenofovir disoproxil fumarate". . p. 336 - 340. Retrieved 2013/07/25.