Methotrexate Dimethyl Ester

Base Information

• Chemical Name: Methotrexate Dimethyl Ester
• CAS No.: 34378-65-9
• Molecular Formula: C22H26N8O5
• Molecular Weight: 482.499
• UNII: 069DRA2V4U
• DSSTox Substance ID: DTXSID60955926
• Nikkaji Number: J558.272E
• ChEMBL ID: CHEMBL3245816
• Mol file: 34378-65-9.mol

Synonyms:Methotrexate Dimethyl Ester;34378-65-9;Dimethyl methotrexate;069DRA2V4U;CHEMBL3245816;dimethyl (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioate;UNII-069DRA2V4U;SCHEMBL19918280;DTXSID60955926;BDBM50290153;METHOTREXATE IMPURITY J [EP IMPURITY];Q27236188;(S)-Dimethyl 2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate;Dimethyl (2S)-2-[[4-[[(2,4-Diaminopteridin-6-yl)methyl]methylamino]benzoyl]amino]pentanedioate (Methotrexate Dimethyl Ester);Dimethyl N-(4-{[(4-amino-2-imino-2,3-dihydropteridin-6-yl)methyl](methyl)amino}benzoyl)glutamate;Glutamic acid, N-(p-(((2,4-diamino-6- pteridinyl)methyl)methylamino)benzoyl)-, dimethyl ester, L-(+)-;L-GLUTAMIC ACID, N-(4-(((2,4-DIAMINO-6-PTERIDINYL)METHYL)METHYLAMINO)BENZOYL)-, 1,5-DIMETHYL ESTER

Chemical Property of Methotrexate Dimethyl Ester

Chemical Property:

• Melting Point: 134-140°C
• PSA: 188.54000
• Density: 1.392g/cm³
• LogP: 1.99850
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 11
• Exact Mass: 482.20261596
• Heavy Atom Count: 35
• Complexity: 735

Purity/Quality:

97% ^*data from raw suppliers

MethotrexateDimethylEster ^*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)NC(CCC(=O)OC)C(=O)OC
• Isomeric SMILES: CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)OC)C(=O)OC
• Uses: Methotrexate EP Impurity J

Technology Process of Methotrexate Dimethyl Ester

There total 12 articles about Methotrexate Dimethyl Ester 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: 77.0%

methanol (67-56-1) + methotrexate (60388-53-6) → methotrexate dimethyl ester (34378-65-9)

Guidance literature:

With boron trifluoride diethyl etherate; for 3.5h; Heating;

DOI:10.1002/jps.2600760810

Reference yield: 73.0%

methanol (67-56-1) + N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid (59-05-2) → dimethyl N-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzoyl)-L-glutamate (34378-65-9) + γ-methyl N'-<4--N-methylamino>benzoyl>-L-glutamate (67022-39-3)

Guidance literature:

With sodium sulfate; tetrafluoroboric acid diethyl ether; for 18h; Ambient temperature;

DOI:10.1021/jm00131a003

Reference yield:

4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid (19741-14-1) + L-glutamic dimethyl ester hydrochloride (23150-65-4) → dimethyl N-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzoyl)-L-glutamate (34378-65-9)

Guidance literature:

4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid; With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 21 ℃; for 0.5h; Inert atmosphere;

L-glutamic dimethyl ester hydrochloride; In N,N-dimethyl-formamide; at 21 ℃; for 5h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b01775

upstream raw materials:

methanol

methotrexate

N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid

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

Downstream raw materials:

7-cyanomethotrexate dimethyl ester

(+/-)-7-hydroxymethotrexate

γ-methyl N'-<4--N-methylamino>benzoyl>-L-glutamate

C₃₄H₃₂N₁₀O₇