Dimethyl 2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)malonate

Base Information

• Chemical Name: Dimethyl 2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)malonate
• CAS No.: 172529-93-0
• Molecular Formula: C12H14ClN5O4
• Molecular Weight: 327.727
• Hs Code.: 2933990090
• European Community (EC) Number: 473-300-6,605-637-3,605-638-9
• DSSTox Substance ID: DTXSID90433242
• Nikkaji Number: J1.167.742H
• Wikidata: Q72468893
• Mol file: 172529-93-0.mol

Synonyms:172529-93-0;Dimethyl 2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)malonate;[2-(2-Amino-6-chloro-9H-purin-9-yl)ethyl]propanedioic acid dimethyl ester;dimethyl 2-[2-(2-amino-6-chloropurin-9-yl)ethyl]propanedioate;DIMETHYL [2-(2-AMINO-6-CHLORO-9H-PURIN-9-YL)ETHYL]MALONATE;EC 605-637-3;1,3-Dimethyl 2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)propanedioate;1,3-dimethyl 2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]propanedioate;AMY377;SCHEMBL4950742;DTXSID90433242;SALNWJHEVGXTER-UHFFFAOYSA-N;BCP11982;FT-0701259;Dimethyl-2-[2-amino-6-chloropurine-9-yl)ethyl]malonate;dimethyl 2-[2-(2-amino-6-chloropurin-9-yl)ethyl]malonate;Dimethyl2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)malonate;Dimethyl [2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]propanedioate;DIMETHYL-2-[2-AMINO-6-CHLOROPURINE-9-YL)ETHYL] MALONATE;2-[2-(2-Amino-6-chloro-9H-purine-9-yl)ethyl]malonic acid dimethyl ester

Chemical Property of Dimethyl 2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)malonate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 115-116 °C
• Refractive Index: 1.666
• Boiling Point: 557.044 °C at 760 mmHg
• Flash Point: 290.69 °C
• PSA: 122.22000
• Density: 1.594 g/cm³
• LogP: 0.99540
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 327.0734316
• Heavy Atom Count: 22
• Complexity: 410

Purity/Quality:

99.9% ^*data from raw suppliers

Dimethyl2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)malonate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CCN1C=NC2=C1N=C(N=C2Cl)N)C(=O)OC
• Uses: Dimethyl 2-[2-(2-amino-6-chloropurin-9-yl)ethyl]malonate is an impurity of Valacyclovir (V085000), a L-Valine ester prodrug of Acyclovir.

Technology Process of Dimethyl 2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)malonate

There total 5 articles about Dimethyl 2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)malonate 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: 99.0%

2-acetoxy-3-butenenitrile (15667-63-7) + methanephosphonous acid mono-n-butyl ester (67538-56-1) → 3-[n-butoxy(methyl)phosphoryl]-1-cyanopropyl acetate (172529-93-0,167004-78-6)

Guidance literature:

With tert-butylperoxy neodecanoate; at 85 ℃; for 4h; Time; Inert atmosphere;

Reference yield: 98.6%

2-acetoxy-3-butenenitrile (15667-63-7) + butyl methylphosphinate (6172-80-1) → 3-[n-butoxy(methyl)phosphoryl]-1-cyanopropyl acetate (172529-93-0,167004-78-6)

Guidance literature:

butyl methylphosphinate; at 75 - 80 ℃; for 0.25h; Inert atmosphere;

2-acetoxy-3-butenenitrile; at 75 - 80 ℃; Temperature; Reagent/catalyst;

Reference yield:

triethyl 3-bromopropane-1,1,1-tricarboxylate (71170-82-6) → 2-amino-6-chloro-9-(3,3-dimethoxycarbonyl-1-propyl)purine (172529-93-0)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 80 °C

2: methanol / 20 °C

With potassium carbonate; In methanol; N,N-dimethyl-formamide;

upstream raw materials:

triethyl 3-bromopropane-1,1,1-tricarboxylate

sodium methylate

2-Amino-6-chloropurin

2-acetoxy-3-butenenitrile

Downstream raw materials:

ammonium glufosinate

Penciclovir

9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine

9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Refernces

• 1、 -. "Method for tubular continuous synthesis of (3-acetoxy-3-cyanopropyl)-methyl phosphinic acid alkyl ester". Paragraph 0053-0060. . Retrieved 2021/06/23.
• 2、 -. "Method for synthesizing 3-(butoxy methyl phosphoryl)-1-cyanopropyl acetate based on micro-channel reactor". Paragraph 0018-0023. . Retrieved 2020/12/31.