Benzamide, N-[9-[(2R)-2-hydroxypropyl]-9H-purin-6-yl]-

Base Information

• Chemical Name: Benzamide, N-[9-[(2R)-2-hydroxypropyl]-9H-purin-6-yl]-
• CAS No.: 160616-03-5
• Molecular Formula: C15H15N5O2
• Molecular Weight: 297.316
• DSSTox Substance ID: DTXSID20477694
• Wikidata: Q82310541
• Mol file: 160616-03-5.mol

Synonyms:160616-03-5;(R)-N-(9-(2-Hydroxypropyl)-9H-purin-6-yl)benzamide;N-[9-[(2R)-2-Hydroxypropyl]-9H-purin-6-yl]benzamide;N-{9-[(2R)-2-hydroxypropyl]-9H-purin-6-yl}benzamide;Benzamide, N-[9-[(2R)-2-hydroxypropyl]-9H-purin-6-yl]-;SCHEMBL7263226;DTXSID20477694;Benzamide, N-[9-(2-hydroxypropyl)-9H-purin-6-yl]-, (R)-

Chemical Property of Benzamide, N-[9-[(2R)-2-hydroxypropyl]-9H-purin-6-yl]-

Chemical Property:

• Melting Point: 223°C
• PSA: 96.42000
• Density: 1.40±0.1 g/cm3(Predicted)
• LogP: 1.84340
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 297.12257474
• Heavy Atom Count: 22
• Complexity: 388

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CN1C=NC2=C(N=CN=C21)NC(=O)C3=CC=CC=C3)O
• Isomeric SMILES: C[C@H](CN1C=NC2=C(N=CN=C21)NC(=O)C3=CC=CC=C3)O
• Uses: N-[9-[(2R)-2-Hydroxypropyl]-9H-purin-6-yl]benzamide is used in the preparation of phosphonomethoxypropyl acyclic nucleotide analogs.

Technology Process of Benzamide, N-[9-[(2R)-2-hydroxypropyl]-9H-purin-6-yl]-

There total 2 articles about Benzamide, N-[9-[(2R)-2-hydroxypropyl]-9H-purin-6-yl]- 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:

(R)-9-<2-(2-tetrahydropyranyloxy)propyl>adenine (160616-02-4) → (R)-9-(2-hydroxypropyl)-N6-benzoyladenine (160616-03-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / sulfuric acid / Ambient temperature

2: 1.) chlorotrimethylsilane / 1) pyridine, room temperature, 1 h; 2) pyridine, room temperature, 2 h

With chloro-trimethyl-silane; sulfuric acid;

DOI:10.1135/cccc19951196

Reference yield:

benzoyl chloride (98-88-4) + (R)-9-(2-hydroxypropyl)adenine (14047-28-0,712-00-5) → (R)-9-(2-hydroxypropyl)-N6-benzoyladenine (160616-03-5)

Guidance literature:

With chloro-trimethyl-silane; Yield given. Multistep reaction; 1) pyridine, room temperature, 1 h; 2) pyridine, room temperature, 2 h;

DOI:10.1135/cccc19951196

Reference yield:

(R)-9-(2-hydroxypropyl)-N6-benzoyladenine (160616-03-5) → tenofovir (147127-20-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / dimethylformamide / 48 h / Ambient temperature

2: sodium methoxide / dimethylformamide / Ambient temperature

3: 47 percent / bromotrimethylsilane / acetonitrile / Ambient temperature

With trimethylsilyl bromide; sodium methylate; sodium hydride; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1135/cccc19951196

upstream raw materials:

benzoyl chloride

(R)-9-(2-hydroxypropyl)adenine

(R)-9-<2-(2-tetrahydropyranyloxy)propyl>adenine

Downstream raw materials:

[(R)-2-(6-Benzoylamino-purin-9-yl)-1-methyl-ethoxymethyl]-phosphonic acid diisopropyl ester

tenofovir