Product Name

This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.
  • Name

    Sildenafil

  • EINECS 200-659-6
  • CAS No. 139755-83-2
  • Article Data43
  • CAS DataBase
  • Density 1.39 g/cm3
  • Solubility Slightly soluble in water, methanol; very slightly soluble in ethanol, chloroform
  • Melting Point 187-189 ºC
  • Formula C22H30N6O4S
  • Boiling Point 672.4 ºC at 760 mmHg
  • Molecular Weight 474.584
  • Flash Point 360.5 ºC
  • Transport Information
  • Appearance White crystalline powder
  • Safety 22-24/25-36-26-45-36/37-16-7
  • Risk Codes 36/37/38-39/23/24/25-23/24/25-11
  • Molecular Structure Molecular Structure of 139755-83-2 (Sildenafil)
  • Hazard Symbols Xi,T,F
  • Synonyms 4-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonyl-phenyl]-9-methyl-7-propyl-3,5,8,9-tetrazabicyclo[4.3.0]nona-3,7,10-trien-2-one;Piperazine,1-[[3-(4,7-dihydro-1-methyl-7- oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin- 5-yl)-4-ethoxyphenyl]sulfonyl]-4-methyl-;Serum Albumin Iodine;Sildenafil Mesylate;Hongdenafil (Acetildenafil);
  • PSA 121.80000
  • LogP 2.56750

Synthetic route

4-[2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)-benzamido]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide
200575-15-1

4-[2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)-benzamido]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 120℃; for 0.166667h; Cyclization; microwave irradiation;100%
With potassium tert-butylate In tert-butyl alcohol for 8h; Reflux;44%
With sodium hydroxide In water for 8h; Reflux;280 mg
1-methyl-piperazine
109-01-3

1-methyl-piperazine

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

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

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With pyridine In water at 50℃; Reagent/catalyst; Temperature;93.9%
With triethylamine In methanol at 20℃; for 0.75h; Product distribution / selectivity;91%
In acetone at 20℃; for 3h; Sealed tube;90%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

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

1-methylpiperazine hydrochloride
34352-59-5, 50398-09-9, 51545-09-6

1-methylpiperazine hydrochloride

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With triethylamine; N-ethyl-N,N-diisopropylamine In water at 60℃; for 1.2h;91.8%
7-chloro-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine
1033861-39-0

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

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Stage #1: 7-chloro-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine With water; sodium hydrogencarbonate In tert-butyl alcohol at 90℃; for 1.5 - 2h; Heating / reflux;
Stage #2: With hydrogenchloride In water at 0℃; pH=8.5 - 9.5; Product distribution / selectivity;		90%
Stage #1: 7-chloro-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine With water; sodium hydrogencarbonate In tert-butyl alcohol for 2h; Reflux;
Stage #2: With hydrogenchloride In water pH=8.5 - 9.5; Product distribution / selectivity;		90%
With water for 4h; Product distribution / selectivity; Heating / reflux;83%
Stage #1: 7-chloro-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine With hydrogenchloride; water at 60℃; for 2h;
Stage #2: With sodium hydrogencarbonate In water at 0℃; pH=8.5 - 9.5; Product distribution / selectivity;		79%
7-bromo-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine
1033861-54-9

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

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Stage #1: 7-bromo-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine With water; sodium hydrogencarbonate In tert-butyl alcohol for 2h; Heating / reflux;
Stage #2: With hydrogenchloride In water at 0℃; pH=8.5 - 9.5; Product distribution / selectivity;		75%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

4-(5-chlorosulfonyl-2-ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide
226956-42-9

4-(5-chlorosulfonyl-2-ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Stage #1: 1-methyl-piperazine; 4-(5-chlorosulfonyl-2-ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide In dichloromethane for 2h;
Stage #2: With potassium carbonate In isopropyl alcohol for 4h; Reagent/catalyst; Reflux;		71.7%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

5-(2-ethoxy-5-iodophenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one
1491216-01-3

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

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Stage #1: 5-(2-ethoxy-5-iodophenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one With 1,10-Phenanthroline; potassium pyrosulfite; tetraethylammonium bromide; sodium formate; palladium diacetate; triphenylphosphine In dimethyl sulfoxide at 70℃; for 2h; Inert atmosphere; Microwave irradiation;
Stage #2: 1-methyl-piperazine With N-Bromosuccinimide In tetrahydrofuran; dimethyl sulfoxide at 0 - 23℃; for 0.5h; Inert atmosphere; chemoselective reaction;		50%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

5-(5-bromo-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one
147676-70-8

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

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Stage #1: 5-(5-bromo-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one With 1,10-Phenanthroline; potassium pyrosulfite; tetraethylammonium bromide; sodium formate; palladium diacetate; triphenylphosphine In dimethyl sulfoxide at 70℃; for 3h; Inert atmosphere; Microwave irradiation;
Stage #2: 1-methyl-piperazine With N-Bromosuccinimide In tetrahydrofuran; dimethyl sulfoxide at 0 - 23℃; for 0.5h; Inert atmosphere; chemoselective reaction;		37%
ethyl 2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)-benzimidate
383427-84-7

ethyl 2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)-benzimidate

4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide
139756-02-8

4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

A

4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamine

4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamine

B

viagra
139755-83-2

viagra

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene; ethyl acetateA 22.6%
B n/a
...Expand
1-methyl-piperazine
109-01-3

1-methyl-piperazine

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

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

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With chlorosulfonic acid 1), 2) EtOH; Multistep reaction;
5-[2-ethoxycarbonyloxy-5-(4-methyl-piperazine-1-sulfonyl)-phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
960009-37-4

5-[2-ethoxycarbonyloxy-5-(4-methyl-piperazine-1-sulfonyl)-phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

ethanol
64-17-5

ethanol

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide at 110℃; under 1324.03 - 2942.29 Torr; for 6h;
With dicyclohexyl-carbodiimide at 105 - 110℃; under 1324.03 - 2942.29 Torr;
1-methyl-piperazine
109-01-3

1-methyl-piperazine

Merrifield resin-OC(O)CH2CH2CH(OH)CH2I

Merrifield resin-OC(O)CH2CH2CH(OH)CH2I

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: iPr2NEt / dimethylformamide
2.1: dimethylformamide / 60 °C
2.2: polymer-supported HOBt; PyBrOP / dimethylformamide
2.3: isocyanate resin / tetrahydrofuran
3.1: 100 percent / NaOEt / ethanol / 0.17 h / 120 °C / microwave irradiation
View Scheme
5-chlorosulfonyl-2-hydroxybenzoic acid
17243-13-9

5-chlorosulfonyl-2-hydroxybenzoic acid

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: iPr2NEt / dimethylformamide
2.1: dimethylformamide / 60 °C
2.2: polymer-supported HOBt; PyBrOP / dimethylformamide
2.3: isocyanate resin / tetrahydrofuran
3.1: 100 percent / NaOEt / ethanol / 0.17 h / 120 °C / microwave irradiation
View Scheme
4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide
139756-02-8

4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dimethylformamide / 60 °C
1.2: polymer-supported HOBt; PyBrOP / dimethylformamide
1.3: isocyanate resin / tetrahydrofuran
2.1: 100 percent / NaOEt / ethanol / 0.17 h / 120 °C / microwave irradiation
View Scheme
Multi-step reaction with 3 steps
1: Et3N, DMAP / CH2Cl2
2: NaOH / ethanol; H2O
3: 1) ClSO3H / 1), 2) EtOH
View Scheme
Multi-step reaction with 3 steps
1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane
2: sodium hydroxide / diethylene glycol
3: triethylamine / toluene / 70 - 75 °C
View Scheme
[N'-(1-cyano-butyl)-N-methyl-hydrazino]-acetic acid ethyl ester
304435-81-2

[N'-(1-cyano-butyl)-N-methyl-hydrazino]-acetic acid ethyl ester

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 90 percent / MnO2
2.1: 90 percent / polymer-supported BEMP / ethanol
3.1: NH3
4.1: dimethylformamide / 60 °C
4.2: polymer-supported HOBt; PyBrOP / dimethylformamide
4.3: isocyanate resin / tetrahydrofuran
5.1: 100 percent / NaOEt / ethanol / 0.17 h / 120 °C / microwave irradiation
View Scheme
[N'-(1-cyano-butylidene)-N-methyl-hydrazino]-acetic acid ethyl ester

[N'-(1-cyano-butylidene)-N-methyl-hydrazino]-acetic acid ethyl ester

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 90 percent / polymer-supported BEMP / ethanol
2.1: NH3
3.1: dimethylformamide / 60 °C
3.2: polymer-supported HOBt; PyBrOP / dimethylformamide
3.3: isocyanate resin / tetrahydrofuran
4.1: 100 percent / NaOEt / ethanol / 0.17 h / 120 °C / microwave irradiation
View Scheme
4-amino-2-methyl-5-propyl-2H-pyrazole-3-carboxylic acid ethyl ester
304435-83-4

4-amino-2-methyl-5-propyl-2H-pyrazole-3-carboxylic acid ethyl ester

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: NH3
2.1: dimethylformamide / 60 °C
2.2: polymer-supported HOBt; PyBrOP / dimethylformamide
2.3: isocyanate resin / tetrahydrofuran
3.1: 100 percent / NaOEt / ethanol / 0.17 h / 120 °C / microwave irradiation
View Scheme
2-hydroxy-5-(4-methylpiperazin-1-ylsulphonyl)benzoic acid
960009-35-2

2-hydroxy-5-(4-methylpiperazin-1-ylsulphonyl)benzoic acid

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dimethylformamide / 60 °C
1.2: polymer-supported HOBt; PyBrOP / dimethylformamide
1.3: isocyanate resin / tetrahydrofuran
2.1: 100 percent / NaOEt / ethanol / 0.17 h / 120 °C / microwave irradiation
View Scheme
Multi-step reaction with 3 steps
1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane
2: sodium hydroxide / diethylene glycol
3: triethylamine / toluene / 70 - 75 °C
View Scheme
Multi-step reaction with 4 steps
1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane
2: sodium hydroxide / diethylene glycol
3: triethylamine
4: dicyclohexyl-carbodiimide / 105 - 110 °C / 1324.03 - 2942.29 Torr
View Scheme
2-ethoxybenzoyl chloride
42926-52-3

2-ethoxybenzoyl chloride

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N, DMAP / CH2Cl2
2: NaOH / ethanol; H2O
3: 1) ClSO3H / 1), 2) EtOH
View Scheme
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 1.5 h / 20 °C
2: sodium hydroxide / tert-butyl alcohol / 35 h / 80 - 90 °C
3: chlorosulfonic acid / 12 h / 20 - 30 °C
4: dichloromethane / 20 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / dichloromethane / 2 h
2.1: chlorosulfonic acid; thionyl chloride / dichloromethane / 2 h
3.1: dichloromethane / 2 h
3.2: 4 h / Reflux
View Scheme
4-[(2-ethoxybenzoyl)amino]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide
139756-03-9

4-[(2-ethoxybenzoyl)amino]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOH / ethanol; H2O
2: 1) ClSO3H / 1), 2) EtOH
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / tert-butyl alcohol / 35 h / 80 - 90 °C
2: chlorosulfonic acid / 12 h / 20 - 30 °C
3: dichloromethane / 20 - 30 °C
View Scheme
2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)benzaldehyde
332374-42-2

2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)benzaldehyde

viagra
139755-83-2

viagra

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene; butanone; 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide3.3 g (53%)
4-Amino-1-methyl-3-n-propyl-1H-pyrazole-5-carboxylate

4-Amino-1-methyl-3-n-propyl-1H-pyrazole-5-carboxylate

2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)benzamidine
383427-89-2

2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)benzamidine

viagra
139755-83-2

viagra

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene; toluene
4-[2-Fluoro-5-(4-methyl-1-piperazinylsulphonyl)benzamido]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

4-[2-Fluoro-5-(4-methyl-1-piperazinylsulphonyl)benzamido]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

viagra
139755-83-2

viagra

Conditions
ConditionsYield
In ethanol; hexane; dichloromethane; ethyl acetate
4-[2-Chloro-5-(4-methyl-1-piperazinylsulphonyl)benzamido]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

4-[2-Chloro-5-(4-methyl-1-piperazinylsulphonyl)benzamido]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

viagra
139755-83-2

viagra

Conditions
ConditionsYield
In ethanol
Glauber's salt

Glauber's salt

ethyl 4-((4-ethoxy-3-[1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-onyl]phenyl)sulfonyl)piperazinecarboxylate
226956-41-8

ethyl 4-((4-ethoxy-3-[1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-onyl]phenyl)sulfonyl)piperazinecarboxylate

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With aq. sodium hydroxide; sodium chloride In tetrahydrofuran; dichloromethane
5-chloro-1-methyl-3-propyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one
1033443-96-7

5-chloro-1-methyl-3-propyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one

[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)]phenylboronic acid
1093065-12-3

[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)]phenylboronic acid

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With sodium carbonate; palladium diacetate; triphenylphosphine In 1,2-dimethoxyethane; water Suzuki Coupling; Inert atmosphere; Reflux;
5-[2-ethoxy-5-(4-methylpiperazin-1-yl-sulphonyl)phenyl]-1-methyl-3-n-propyl-1-hydro-7-ethoxypyrazolo[4,3-d]pyrimidine
1093065-15-6

5-[2-ethoxy-5-(4-methylpiperazin-1-yl-sulphonyl)phenyl]-1-methyl-3-n-propyl-1-hydro-7-ethoxypyrazolo[4,3-d]pyrimidine

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Stage #1: 5-[2-ethoxy-5-(4-methylpiperazin-1-yl-sulphonyl)phenyl]-1-methyl-3-n-propyl-1-hydro-7-ethoxypyrazolo[4,3-d]pyrimidine With hydrogenchloride; water In methanol at 75℃; for 4.5h;
Stage #2: With sodium hydroxide In methanol; water pH=14;
5-[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl]-7-methoxy-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidine
864164-45-4

5-[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl]-7-methoxy-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidine

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Stage #1: 5-[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl]-7-methoxy-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidine With hydrogenchloride; water In methanol at 75℃; for 4h;
Stage #2: With sodium hydroxide In methanol; water pH=14;
ethyl bromide
74-96-4

ethyl bromide

5-[2-hydroxy-5-(4-methylpiperazine-1-ylsulphonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

5-[2-hydroxy-5-(4-methylpiperazine-1-ylsulphonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With triethylamine In toluene at 70 - 75℃;49 %Chromat.
viagra
139755-83-2

viagra

citric acid
77-92-9

citric acid

sildenafil citrate

sildenafil citrate

Conditions
ConditionsYield
In methanol; toluene for 1h; Product distribution / selectivity; Heating / reflux;99.7%
In ethanol for 1h; Product distribution / selectivity; Heating / reflux;96.2%
In acetone at 55℃; for 0.5h; Reflux;96.52%
viagra
139755-83-2

viagra

sildenafil hydrochloride
252920-86-8

sildenafil hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether for 4h;99%
With hydrogenchloride In propan-1-ol; acetone for 2h; Product distribution / selectivity; Heating / reflux;
With hydrogenchloride In propan-1-ol; toluene for 24h;
With hydrogenchloride In propan-1-ol for 1h; Product distribution / selectivity; Heating / reflux;
viagra
139755-83-2

viagra

1-[[3-(6,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-methyl-4-oxido-piperazine
1094598-75-0

1-[[3-(6,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-methyl-4-oxido-piperazine

Conditions
ConditionsYield
Stage #1: viagra With 3-chloro-benzenecarboperoxoic acid In dichloromethane; water at -10℃; for 2.5h;
Stage #2: With potassium carbonate In dichloromethane; water at 0℃; for 0.5h;		92%
viagra
139755-83-2

viagra

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

4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonic acid

Conditions
ConditionsYield
With sulfuric acid; water at 20 - 100℃; for 41h;50%
Chloromethyl acetate
625-56-9

Chloromethyl acetate

viagra
139755-83-2

viagra

1-(acetoxymethyl)-4-((4-ethoxy-3-(1-methyl-7-oxo-3-propyl-4,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)sulfonyl)-1-methylpiperazin-1-ium iodide
1402916-50-0

1-(acetoxymethyl)-4-((4-ethoxy-3-(1-methyl-7-oxo-3-propyl-4,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)sulfonyl)-1-methylpiperazin-1-ium iodide

Conditions
ConditionsYield
With sodium iodide In acetonitrile at 20℃;42%
acetonitrile
75-05-8

acetonitrile

viagra
139755-83-2

viagra

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine hydrogensulphate acetonitrile solvate

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine hydrogensulphate acetonitrile solvate

Conditions
ConditionsYield
With sulfuric acid In water for 1h; Heating / reflux;
ethanol
64-17-5

ethanol

viagra
139755-83-2

viagra

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine hydrogensulphate hemiethanol solvate

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine hydrogensulphate hemiethanol solvate

Conditions
ConditionsYield
With sulfuric acid at 20℃; Heating / reflux;
viagra
139755-83-2

viagra

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine hemisulphate

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine hemisulphate

Conditions
ConditionsYield
With sulfuric acid In toluene at 20 - 50℃; for 72.5h;
L-Tartaric acid
87-69-4

L-Tartaric acid

viagra
139755-83-2

viagra

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine hemitartrate

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine hemitartrate

Conditions
ConditionsYield
In ethanol at 20℃; for 13h; Heating / reflux;
ethanesulfonic acid
594-45-6

ethanesulfonic acid

viagra
139755-83-2

viagra

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine esylate

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine esylate

Conditions
ConditionsYield
In acetonitrile at 20℃; for 1 - 2h; Product distribution / selectivity; Heating / reflux;
In acetonitrile at 20℃; for 13h; Heating / reflux;
(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

viagra
139755-83-2

viagra

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine fumarate

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine fumarate

Conditions
ConditionsYield
In ethanol; acetonitrile at 20℃; for 14h; Heating / reflux;

Sildenafil History

 Sildenafil (CAS NO.139755-83-2) (compound UK-92,480) was synthesized by a group of pharmaceutical chemists working at Pfizer's Sandwich, Kent, research facility in England. It was initially studied for use in hypertension (high blood pressure) and angina pectoris (a symptom of ischaemic heart disease).

Sildenafil Specification

Sildenafil(CAS NO.139755-83-2), its Synonyms are 1-((3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-d)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine; Revatio; Viagra; Piperazine, 1-((3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-d)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methyl-. It is a drug used to treat erectile dysfunction and pulmonary arterial hypertension (PAH). It acts by inhibiting cGMP specific phosphodiesterase type 5, an enzyme that regulates blood flow in the penis.

Physical properties about Sildenafil are: (1)ACD/LogP: 2.468; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 1.83; (4)ACD/LogD (pH 7.4): 2.45; (5)ACD/BCF (pH 5.5): 10.24 ; (6)ACD/BCF (pH 7.4): 42.36; (7)ACD/KOC (pH 5.5): 121.40; (8)ACD/KOC (pH 7.4): 502.20; (9)#H bond acceptors: 10; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.665; (13)Molar Refractivity: 126.026 cm3; (14)Molar Volume: 339.438 cm3; (15)Polarizability: 49.961 10-24cm3; (16)Surface Tension: 54.4710006713867 dyne/cm; (17)Density: 1.398 g/cm3; (18)Flash Point: 360.5 °C; (19)ES27:Take off immediately all contaminated clothing. nthalpy of Vaporization: 98.77 kJ/mol; (20)Boiling Point: 672.4 °C at 760 mmHg; (21)Vapour Pressure: 6.1E-18 mmHg at 25°C

When you are using Sildenafil, please be cautious about it as the following:
1. Do not breathe dust;
2. Avoid contact with skin and eyes;
3. Wear suitable protective clothing;
4. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C22H30N6O4S/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29) ;
(2)InChIKey=BNRNXUUZRGQAQC-UHFFFAOYSA-N; (3)Smilesc1(c2nc3c(c(=O)[nH]2)n(nc3CCC)C)c(ccc(c1)S(=O)(=O)N1CCN(CC1)C)OCC

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