7-Hydroxymethotrexate

Base Information

• Chemical Name: 7-Hydroxymethotrexate
• CAS No.: 5939-37-7
• Molecular Formula: C20H22 N8 O6
• Molecular Weight: 470.445
• UNII: X019Z9S1DL
• DSSTox Substance ID: DTXSID70891503
• Nikkaji Number: J387.912G
• Wikidata: Q27293136
• ChEMBL ID: CHEMBL3544661
• Mol file: 5939-37-7.mol

Synonyms:7-hydroxymethotrexate;7-OH-methotrexate

Chemical Property of 7-Hydroxymethotrexate

Chemical Property:

• Melting Point: 230ºC dec.
• Refractive Index: 1.6910 (estimate)
• Boiling Point: 571.95°C (rough estimate)
• PSA: 230.77000
• Density: 1.68g/cm³
• LogP: 1.52730
• Storage Temp.: −20°C
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 9
• Exact Mass: 470.16623045
• Heavy Atom Count: 34
• Complexity: 830

Purity/Quality:

99%, ^*data from raw suppliers

7-HydroxyMethotrexate 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(CC1=NC2=C(N=C(N=C2NC1=O)N)N)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O
• Isomeric SMILES: CN(CC1=NC2=C(N=C(N=C2NC1=O)N)N)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O
• Uses: 7-Hydroxy Methotrexate is a metabolite of Methotrexate, which is used as a antineoplastic and antirheumatic.

Technology Process of 7-Hydroxymethotrexate

There total 3 articles about 7-Hydroxymethotrexate 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: 47.0%

7-cyanomethotrexate dimethyl ester (112163-39-0) → (+/-)-7-hydroxymethotrexate (5939-37-7)

Guidance literature:

With sodium hydroxide; water; In tetrahydrofuran; at 4 ℃; for 23h;

DOI:10.1002/jps.2600760810

Reference yield:

methotrexate dimethyl ester (34378-65-9) → (+/-)-7-hydroxymethotrexate (5939-37-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / Et₃N, H₂O / acetonitrile / 18 h / Ambient temperature

2: 47 percent / H₂O, 1M NaOH / tetrahydrofuran / 23 h / 4 °C

With sodium hydroxide; water; triethylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1002/jps.2600760810

Reference yield:

methotrexate (60388-53-6) → (+/-)-7-hydroxymethotrexate (5939-37-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / BF₃*Et₂O / 3.5 h / Heating

2: 86 percent / Et₃N, H₂O / acetonitrile / 18 h / Ambient temperature

3: 47 percent / H₂O, 1M NaOH / tetrahydrofuran / 23 h / 4 °C

With sodium hydroxide; boron trifluoride diethyl etherate; water; triethylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1002/jps.2600760810

upstream raw materials:

7-cyanomethotrexate dimethyl ester

methotrexate dimethyl ester

methotrexate

Refernces