5-(5-Chlorosulfonyl-2-ethoxyphenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Base Information

• Chemical Name: 5-(5-Chlorosulfonyl-2-ethoxyphenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
• CAS No.: 139756-22-2
• Molecular Formula: C17H19ClN4O4S
• Molecular Weight: 410.881
• Hs Code.: 2933990090
• Mol file: 139756-22-2.mol

Synonyms:4-ethoxy-3-(1-methyl-7-oxo-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonyl chloride

Chemical Property of 5-(5-Chlorosulfonyl-2-ethoxyphenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Chemical Property:

• Appearance/Colour: Off-White to Pale Beige Solid
• Vapor Pressure: 2.29E-15mmHg at 25°C
• Melting Point: 180-182°C
• Refractive Index: 1.663
• Boiling Point: 621.4ºC at 760 mmHg
• PKA: 9.87±0.20(Predicted)
• Flash Point: 329.6ºC
• PSA: 115.32000
• Density: 1.48g/cm3
• LogP: 3.68310
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

99.9% ^*data from raw suppliers

5-(5-Chlorosulfonyl-2-ethoxyphenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Sildenafil derivative Sildenafil derivative.

Technology Process of 5-(5-Chlorosulfonyl-2-ethoxyphenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

There total 23 articles about 5-(5-Chlorosulfonyl-2-ethoxyphenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one 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: 97.0%

5-(2-ethoxy)-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidine-7-one (139756-21-1) → 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (139756-22-2)

Guidance literature:

With chlorosulfonic acid; at 0 - 25 ℃; for 2h;

DOI:10.1021/jm701400r

Reference yield:

4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonic acid (1357931-55-5) → 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (139756-22-2)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 ℃; for 5h; Inert atmosphere;

Reference yield:

4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide (139756-02-8) → 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (139756-22-2)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 20 °C

2: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C

3: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice

With chlorosulfonic acid; dihydrogen peroxide; triethylamine; sodium hydroxide; In ethanol; dichloromethane; water;

upstream raw materials:

5-(2-ethoxy)-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidine-7-one

ethyl 3-butyrylpyruvate

2-Pentanone

ethyl 3-propyl-1H-pyrazole-5-carboxylate

Downstream raw materials:

5-[2-ethoxy-5-[4-(2-hydroxyethyl)-1-piperazinyl-sulphonyl]phenyl}-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

C₂₇H₃₈N₆O₄S

C₂₇H₃₂N₆O₄S

C₂₇H₃₁ClN₆O₄S

Refernces

• 1、 Laha, Joydev K.,Gulati, Upma,Saima,Gupta, Anjali,Indurthi, Harish Kumar. "Improved, gram-scale synthesis of sildenafil in water using arylacetic acid as the acyl source in the pyrazolo[4,3-d]pyrimidin-7-one ring formation". supporting information. p. 2643 - 2648. Retrieved 2021/02/16.
• 2、 -. "Improved synthesis process of sildenafil". Paragraph 0039-0042; 0048-0049. . Retrieved 2021/06/21.