4-((2,4-Diaminopyrimidin-5-yl)methyl)-2,6-dimethoxyphenol

Base Information

• Chemical Name: 4-((2,4-Diaminopyrimidin-5-yl)methyl)-2,6-dimethoxyphenol
• CAS No.: 21253-58-7
• Molecular Formula: C13H16N4O3
• Molecular Weight: 276.295
• UNII: N775B87UF5
• DSSTox Substance ID: DTXSID90877223
• Nikkaji Number: J516.948H
• Wikidata: Q82858974
• ChEMBL ID: CHEMBL1181
• Mol file: 21253-58-7.mol

Synonyms:21253-58-7;4-Demethyltrimethoprim;4-((2,4-Diaminopyrimidin-5-yl)methyl)-2,6-dimethoxyphenol;4-HYDROXYTRIMETHOPRIM;4'-Hydroxytrimethoprim;4-Demethyl-trimethoprim;CHEMBL1181;4-[(2,4-diaminopyrimidin-5-yl)methyl]-2,6-dimethoxyphenol;N775B87UF5;2,4-diamino-5-(3,5-dimethoxy-4-hydroxybenzyl)pyrimidine;RO 5-9552/001;4-((2,4-Diamino-5-pyrimidinyl)methyl)-2,6-dimethoxyphenol;2,4-diamino-5-(3',5'-dimethoxy-4'-hydroxybenzyl)-pyrimidine;Phenol, 4-((2,4-diamino-5-pyrimidinyl)methyl)-2,6-dimethoxy-;4'-O-Demethyltrimetoprim;SCHEMBL248638;UNII-N775B87UF5;AMY9086;DTXSID90877223;HPOCGNHBIFZCAN-UHFFFAOYSA-N;BDBM50404462;E80333;2,4-NH2PYRIMIDINE,5(35MEO-4-OH)BENZYL;2,4-diamino-5-(4-hydroxy-3,5-dimethoxybenzyl)pyrimidine;2,4-diamino-5-(3',5'-dimethoxy-4'-hydroxybenzyl)pyrimidine

Chemical Property of 4-((2,4-Diaminopyrimidin-5-yl)methyl)-2,6-dimethoxyphenol

Chemical Property:

• Melting Point: 265-270 °C (decomp)
• Boiling Point: 567.4±60.0 °C(Predicted)
• PKA: 9.88±0.25(Predicted)
• Density: 1.339±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 276.12224039
• Heavy Atom Count: 20
• Complexity: 293

Purity/Quality:

97% ^*data from raw suppliers

4-Demethyltrimethoprim ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)OC)CC2=CN=C(N=C2N)N
• Uses: 4-Demethyltrimethoprim is an impurity of Trimethoprim (T795615), an antibacterial agent.

Technology Process of 4-((2,4-Diaminopyrimidin-5-yl)methyl)-2,6-dimethoxyphenol

There total 4 articles about 4-((2,4-Diaminopyrimidin-5-yl)methyl)-2,6-dimethoxyphenol 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: 75.0%

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine (738-70-5) → 2,4-diamino-5-(3,5-dimethoxy-4-hydroxybenzyl)pyrimidine (21253-58-7)

Guidance literature:

With hydrogen bromide; In water; at 100 ℃; for 0.25h;

DOI:10.1016/bs.mie.2020.03.015

Reference yield: 35.0%

2,4-diaminopyrimidine (156-81-0) + 2,6-dimethoxy-4-<(N,N-dimethylamino)methyl>phenol (39667-14-6) → bis(4-hydroxy-2,6-dimethoxyphenyl)methane (15640-40-1) + 2,4-diamino-5-(3,5-dimethoxy-4-hydroxybenzyl)pyrimidine (21253-58-7)

Guidance literature:

In ethylene glycol; at 140 - 160 ℃;

DOI:10.1021/jm00178a007

Reference yield:

5-(4-Hydroxy-3,5-dimethoxy-benzyl)-pyrimidine-2,4-diol → 2,4-diamino-5-(3,5-dimethoxy-4-hydroxybenzyl)pyrimidine (21253-58-7)

Guidance literature:

With ammonia; trichlorophosphate; Yield given. Multistep reaction; 1.) reflux, 2 h, 2.) EtOH, 160 deg C, 9 h;

DOI:10.1021/jm00178a007

upstream raw materials:

2,4-diaminopyrimidine

2,6-dimethoxy-4-<(N,N-dimethylamino)methyl>phenol

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Downstream raw materials:

5-[4-(2,4-Diamino-pyrimidin-5-ylmethyl)-2,6-dimethoxy-phenoxy]-pentanoic acid methyl ester

4-[4-(2,4-Diamino-pyrimidin-5-ylmethyl)-2,6-dimethoxy-phenoxy]-butyric acid ethyl ester

6-[4-(2,4-Diamino-pyrimidin-5-ylmethyl)-2,6-dimethoxy-phenoxy]-hexanoic acid methyl ester

5-{3,5-Dimethoxy-4-[4-(4-nitro-benzenesulfonyl)-benzyloxy]-benzyl}-pyrimidine-2,4-diamine