methyl 4-({4-[(2,6-diamino-5-nitropyrimidin-4-yl)amino]-3-oxobutyl}sulfanyl)benzoate

Base Information

• Chemical Name: methyl 4-({4-[(2,6-diamino-5-nitropyrimidin-4-yl)amino]-3-oxobutyl}sulfanyl)benzoate
• CAS No.: 74163-02-3
• Molecular Formula: C16H18 N6 O5 S
• Molecular Weight: 406.4163
• Mol file: 74163-02-3.mol

Synonyms:NSC 319974

Chemical Property of methyl 4-({4-[(2,6-diamino-5-nitropyrimidin-4-yl)amino]-3-oxobutyl}sulfanyl)benzoate

Chemical Property:

• Vapor Pressure: 1.25E-22mmHg at 25°C
• Boiling Point: 754.1°Cat760mmHg
• Flash Point: 409.9°C
• Density: 1.48g/cm³

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl 4-({4-[(2,6-diamino-5-nitropyrimidin-4-yl)amino]-3-oxobutyl}sulfanyl)benzoate

There total 5 articles about methyl 4-({4-[(2,6-diamino-5-nitropyrimidin-4-yl)amino]-3-oxobutyl}sulfanyl)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: 94.0%

4-(2-{2-[(2,6-Diamino-5-nitro-pyrimidin-4-ylamino)-methyl]-[1,3]dioxolan-2-yl}-ethylsulfanyl)-benzoic acid methyl ester (74163-01-2) → 4-[4-(2,6-Diamino-5-nitro-pyrimidin-4-ylamino)-3-oxo-butylsulfanyl]-benzoic acid methyl ester (74163-02-3)

Guidance literature:

With trifluoroacetic acid; at 50 ℃;

DOI:10.1021/jm00182a017

Reference yield:

1-chloro-4--2-butanone (67426-03-3) → 4-[4-(2,6-Diamino-5-nitro-pyrimidin-4-ylamino)-3-oxo-butylsulfanyl]-benzoic acid methyl ester (74163-02-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / sodium azide, potassium iodide / acetone

2: 85 percent / p-toluenesulfonic acid / benzene / 6 h / Heating

3: H₂ / 5percent Pd/C / methanol / 18 h / 1189.4 Torr

4: 78 percent / N-methylmorpholine / methanol / 4 h / Heating

5: 94 percent / trifluoroacetic acid (TFA) / 50 °C

With 4-methyl-morpholine; sodium azide; hydrogen; toluene-4-sulfonic acid; trifluoroacetic acid; potassium iodide; palladium on activated charcoal; In methanol; acetone; benzene;

DOI:10.1021/jm00182a017

Reference yield:

1-azido-4--2-butanone (74162-96-2) → 4-[4-(2,6-Diamino-5-nitro-pyrimidin-4-ylamino)-3-oxo-butylsulfanyl]-benzoic acid methyl ester (74163-02-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / p-toluenesulfonic acid / benzene / 6 h / Heating

2: H₂ / 5percent Pd/C / methanol / 18 h / 1189.4 Torr

3: 78 percent / N-methylmorpholine / methanol / 4 h / Heating

4: 94 percent / trifluoroacetic acid (TFA) / 50 °C

With 4-methyl-morpholine; hydrogen; toluene-4-sulfonic acid; trifluoroacetic acid; palladium on activated charcoal; In methanol; benzene;

DOI:10.1021/jm00182a017

upstream raw materials:

4-(2-{2-[(2,6-Diamino-5-nitro-pyrimidin-4-ylamino)-methyl]-[1,3]dioxolan-2-yl}-ethylsulfanyl)-benzoic acid methyl ester

1-chloro-4--2-butanone

4-[2-(2-Aminomethyl-[1,3]dioxolan-2-yl)-ethylsulfanyl]-benzoic acid methyl ester

1-azido-4--2-butanone

Downstream raw materials:

11-thiohomoaminopterin

4-amino-4-deoxy-11-thiohomopteroic acid

methyl 4-amino-4-deoxy-11-thiohomopteroate

Refernces