Methyl 4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoate

Base Information

• Chemical Name: Methyl 4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoate
• CAS No.: 23853-09-0
• Molecular Formula: C16H17 N7 O2
• Molecular Weight: 339.357
• Hs Code.: 2933990090
• NSC Number: 133722
• DSSTox Substance ID: DTXSID70299929
• Wikidata: Q82042644
• ChEMBL ID: CHEMBL175324
• Mol file: 23853-09-0.mol

Synonyms:23853-09-0;DAMPA Methyl Ester;methyl 4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoate;methyl 4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoate;Benzoic acid,4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]-, methyl ester;Methyl 4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzoate;NSC133722;CHEMBL175324;DTXSID70299929;AKOS030254661;NSC-133722;FT-0665461;J-015237

Chemical Property of Methyl 4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoate

Chemical Property:

• Vapor Pressure: 3.18E-16mmHg at 25°C
• Melting Point: .250°C (dec.)
• Boiling Point: 639°C at 760 mmHg
• PKA: 5.56±0.10(Predicted)
• Flash Point: 340.2°C
• PSA: 133.14000
• Density: 1.428g/cm³
• LogP: 2.16960
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 339.14437281
• Heavy Atom Count: 25
• Complexity: 458

Purity/Quality:

97% ^*data from raw suppliers

DAMPA Methyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)OC
• Uses: A Methotrexate analog with altered ester group.

Technology Process of Methyl 4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoate

There total 5 articles about Methyl 4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoate 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%

6-bromomethyl-pteridine-2,4-diamine (59368-16-0) + methyl 4-(N-methyl)aminobenzoate (18358-63-9) → 4-[(2,4-diaminopteridin-6-ylmethyl)-N-methylamino]benzoic acid methyl ester (23853-09-0)

Guidance literature:

In N,N-dimethyl acetamide; at 70 ℃; for 12h;

DOI:10.1021/jacs.7b09359

Reference yield: 96.0%

6-bromomethylpteridine-2,4-diamine trihydrobromide + methyl 4-(N-methyl)aminobenzoate (18358-63-9) → 4-[(2,4-diaminopteridin-6-ylmethyl)-N-methylamino]benzoic acid methyl ester (23853-09-0)

Guidance literature:

6-bromomethylpteridine-2,4-diamine trihydrobromide; methyl 4-(N-methyl)aminobenzoate; In N,N-dimethyl acetamide; at 60 - 70 ℃; for 24h;

With sodium hydrogencarbonate; In N,N-dimethyl acetamide; at 0 ℃;

DOI:10.1016/j.bmc.2009.04.063

Reference yield:

2,4-diamino-6-(hydroxymethyl)pteridine (945-24-4) → 4-[(2,4-diaminopteridin-6-ylmethyl)-N-methylamino]benzoic acid methyl ester (23853-09-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dibromotriphenylphosphorane / N,N-dimethyl acetamide / 12 h / 25 °C

1.2: 0.5 h / 25 °C

2.1: N,N-dimethyl acetamide / 12 h / 70 °C

With dibromotriphenylphosphorane; In N,N-dimethyl acetamide;

DOI:10.1021/jacs.7b09359

upstream raw materials:

methyl 4-(N-methyl)aminobenzoate

2,4-diamino-6-(hydroxymethyl)pteridine

6-bromomethyl-pteridine-2,4-diamine

N-methyl-p-aminobenzoic acid

Downstream raw materials:

4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid

Refernces

• 1、 Homma, Akie,Sato, Haruhiko,Okamachi, Akira,Emura, Takashi,Ishizawa, Takenori,Kato, Tatsuya,Matsuura, Tetsu,Sato, Shigeo,Tamura, Tatsuya,Higuchi, Yoshinobu,Watanabe, Tomoyuki,Kitamura, Hidetomo,Asanuma, Kentaro,Yamazaki, Tadao,Ikemi, Masahisa,Kitagawa, Hironoshin,Morikawa, Tadashi,Ikeya, Hitoshi,Maeda, Kazuaki,Takahashi, Koichi,Nohmi, Kenji,Izutani, Noriyuki,Kanda, Makoto,Suzuki, Ryochi. "Novel hyaluronic acid-methotrexate conjugates for osteoarthritis treatment". experimental part. p. 4647 - 4656. Retrieved 2009/12/01.