(E)-6-amino-9-(prop-1-en-1-yl)-9H-purine

Base Information

• Chemical Name: (E)-6-amino-9-(prop-1-en-1-yl)-9H-purine
• CAS No.: 1464851-21-5
• Molecular Formula: C₈H₉N₅
• Molecular Weight: 175.193
• Mol file: 1464851-21-5.mol

Synonyms:

Chemical Property of (E)-6-amino-9-(prop-1-en-1-yl)-9H-purine

Chemical Property:

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

Purity/Quality:

98% ^*data from raw suppliers

(Z)-MutagenicImpurityofTenofovirDisoproxil >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-6-amino-9-(prop-1-en-1-yl)-9H-purine

There total 40 articles about (E)-6-amino-9-(prop-1-en-1-yl)-9H-purine 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:

N6-acetyladenine (6034-68-0) → 9-propenyladenine (4121-40-8,1464851-21-5)

Guidance literature:

Multi-step reaction with 3 steps

1: formic acid ethyl ester / 7 h / Reflux

2: sodium hydroxide / water / 2 h / 70 °C

3: lithium ethoxide / tetrahydrofuran; ethanol / 0.5 h / 20 °C

With lithium ethoxide; sodium hydroxide; formic acid ethyl ester; In tetrahydrofuran; ethanol; water; 3: |Wittig Olefination;

upstream raw materials:

ethyltriphenylphosphonium bromide

N⁶-acetyladenine

9-allyl-9H-adenine

adenine

Refernces

• 1、 -. "Preparation method of tenofovir intermediate". Paragraph 0021-0038. . Retrieved 2017/08/28.
• 2、 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.