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330784-47-9

Basic Information
CAS No.: 330784-47-9
Name: 5-Pyrimidinecarboxamide,4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-N-(2-pyrimidinylmethyl)-
Molecular Structure:
Molecular Structure of 330784-47-9 (5-Pyrimidinecarboxamide,4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-N-(2-pyrimidinylmethyl)-)
Formula: C23H26ClN7O3
Molecular Weight: 483.95
Synonyms: (S)-2-(2-Hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[(2-pyrimidinylmethyl)carbamoyl]pyrimidine;TA 1790;
EINECS:
Density: 1.373 g/cm3
Melting Point: 150-152 °C
Boiling Point:
Flash Point:
Solubility:
Appearance: White solid
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 125.39000
LogP: 2.96070
Synthetic route
330785-84-7

4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidine-5-carboxylic acid

75985-45-4

2-aminomethylpyrimidine

330784-47-9

avanafil

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide; 1-hydroxy-1,2,3-benzotriazine-4(3H)-one In N,N-dimethyl-formamide at 0℃; Temperature;99%
With 5, 10, 15, 20-tetrakis[4-(dihydroxyboryl)phenyl]-21H,23H-porphine In toluene for 16h; Time; Reflux; Green chemistry;91.2%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20℃; for 4h;90%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 20℃; for 8h;

2-chloro-4-((3-chloro-4-methoxybenzyl)amino)-N-[pyrimidin-2ylmethyl]pyrimidine-5-carboxamide

23356-96-9

(S)-1-Pyrrolidin-2-yl-methanol

330784-47-9

avanafil

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 20h;97.2%

4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide

23356-96-9

(S)-1-Pyrrolidin-2-yl-methanol

330784-47-9

avanafil

Conditions
ConditionsYield
With 1H-imidazole In toluene at 20℃; for 18h; Solvent; Reagent/catalyst;97%
With triethylamine at 20 - 30℃; for 1h; Solvent;1.1 g

4-[(3-chloro-4-methoxybenzyl)amino]-2-methanesulfonyl-N-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamide

23356-96-9

(S)-1-Pyrrolidin-2-yl-methanol

330784-47-9

avanafil

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In chloroform at 50℃; Temperature;90.5%
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 20℃; for 5h;87.5%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; Temperature; Green chemistry;87%

ethyl (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)tetrahydropyrrole-1-yl)-5-pyrimidinecarboxylate

75985-45-4

2-aminomethylpyrimidine

330784-47-9

avanafil

Conditions
ConditionsYield
Stage #1: ethyl (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)tetrahydropyrrole-1-yl)-5-pyrimidinecarboxylate With dimethyl sulfoxide; citric acid; sodium hydroxide In water for 15h;
Stage #2: 2-aminomethylpyrimidine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 8h;
87%
In dichloromethane at 20℃;44%

6-(3-chloro-4-methoxy-benzylamino)-1,2-dihydropyrimidin-2-one-5-(N-2-methylpyrimidinyl)formamide

23356-96-9

(S)-1-Pyrrolidin-2-yl-methanol

330784-47-9

avanafil

Conditions
ConditionsYield
Stage #1: 6-(3-chloro-4-methoxy-benzylamino)-1,2-dihydropyrimidin-2-one-5-(N-2-methylpyrimidinyl)formamide With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20 - 60℃; for 24h; Inert atmosphere;
Stage #2: (S)-1-Pyrrolidin-2-yl-methanol With sodium hydride In tetrahydrofuran at 65℃; for 5h;
81.3%

4-[(3-chloro-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1-pyrrolidinyl]pyrimidine

N-(2-methylpyrimidine)methanamide

330784-47-9

avanafil

Conditions
ConditionsYield
Stage #1: 4-[(3-chloro-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1-pyrrolidinyl]pyrimidine With bromine; sodium hydroxide for 0.0833333h; Microwave irradiation;
Stage #2: N-(2-methylpyrimidine)methanamide With tris(2,4-di-t-butyl)phenoxy phosphazene; sodium methylate; nickel diacetate In 1,2-dimethoxyethane at 120℃; for 10h; Inert atmosphere;
81.1%
330785-84-7

4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidine-5-carboxylic acid

2-aminomethylpyrimidine methanesulfonate

330784-47-9

avanafil

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 15 - 25℃;67%
1246834-64-9

2-aminomethylpyrimidine acetate

23356-96-9

(S)-1-Pyrrolidin-2-yl-methanol

41965-95-1

(3-chloro-4-methoxyphenyl)methylamine hydrogen chloride

2972-52-3

2,4-dichloropyrimidine-5-carbonyl chloride

330784-47-9

avanafil

Conditions
ConditionsYield
Stage #1: 2-aminomethylpyrimidine acetate; 2,4-dichloropyrimidine-5-carbonyl chloride With triethylamine In dichloromethane for 1h; Cooling with ice;
Stage #2: (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride With triethylamine In dichloromethane for 2h;
Stage #3: (S)-1-Pyrrolidin-2-yl-methanol In dichloromethane at 20℃;
64%

4-(3-chloro-4-methoxybenzylamino)-2-[(S)-2-hydroxymethylpyrrolidinyl-1-yl]-5-pyrimidinecarboxylic acid chloride

75985-45-4

2-aminomethylpyrimidine

330784-47-9

avanafil

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;64%

2-chloro-4-((3-chloro-4-methoxybenzyl)amino)-N-[pyrimidin-2ylmethyl]pyrimidine-5-carboxamide

330784-47-9

avanafil

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; Reagent/catalyst; Solvent; Temperature;61%
330785-84-7

4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidine-5-carboxylic acid

1246834-64-9

2-aminomethylpyrimidine acetate

330784-47-9

avanafil

Conditions
ConditionsYield
Stage #1: 2-aminomethylpyrimidine acetate With triethylamine In N,N-dimethyl-formamide for 0.5h;
Stage #2: 4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidine-5-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 8h;
60%

2,4-dichloro-N-(pyrimidin-2-ylmethyl)-5-pyrimidinecarboxamide

23356-96-9

(S)-1-Pyrrolidin-2-yl-methanol

41965-95-1

(3-chloro-4-methoxyphenyl)methylamine hydrogen chloride

330784-47-9

avanafil

Conditions
ConditionsYield
Stage #1: 2,4-dichloro-N-(pyrimidin-2-ylmethyl)-5-pyrimidinecarboxamide; (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride With triethylamine for 2h;
Stage #2: (S)-1-Pyrrolidin-2-yl-methanol at 20℃; for 4h;
32%
330785-84-7

4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidine-5-carboxylic acid

2-aminomethylpyrimidine acetic acid

330784-47-9

avanafil

Conditions
ConditionsYield
Stage #1: 4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidine-5-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25 - 35℃; for 0.333333h;
Stage #2: 2-aminomethylpyrimidine acetic acid With triethylamine In N,N-dimethyl-formamide at 25 - 35℃; for 9h;
Stage #3: In methanol at 25 - 35℃; for 0.75h;
68 g
330786-34-0

4-[(3-chloro-4-methoxybenzyl)amino]-2-(methylsulfanyl)pyrimidine-5-carboxylic acid

330784-47-9

avanafil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
2: 3-chloro-benzenecarboperoxoic acid / 0 °C
3: 20 - 120 °C
View Scheme
Multi-step reaction with 3 steps
1.1: thionyl chloride / toluene; N,N-dimethyl-formamide / 2.5 h / Reflux
1.2: 15 - 30 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 25 - 30 °C
3.1: triethylamine / dichloromethane
View Scheme
Multi-step reaction with 4 steps
1.1: thionyl chloride / toluene; N,N-dimethyl-formamide / 2.5 h / Reflux
1.2: 15 - 30 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 25 - 30 °C
3.1: triethylamine / dichloromethane
4.1: sulfuric acid / ethanol / Reflux
4.2: 5 h
View Scheme

4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide

330784-47-9

avanafil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid / 0 °C
2: 20 - 120 °C
View Scheme
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 25 - 30 °C
2: triethylamine / dichloromethane
View Scheme
Multi-step reaction with 3 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 25 - 30 °C
2.1: triethylamine / dichloromethane
3.1: sulfuric acid / ethanol / Reflux
3.2: 5 h
View Scheme
Multi-step reaction with 4 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 25 - 30 °C
2.1: triethylamine / dichloromethane
3.1: thionyl chloride / toluene; N,N-dimethyl-formamide / 2.5 h / Reflux
4.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 5 °C
4.2: 60 - 70 °C
View Scheme
5909-24-0

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

330784-47-9

avanafil

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: triethylamine / tetrahydrofuran / 20 °C
2: sodium hydroxide / water; ethanol / 20 °C
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
4: 3-chloro-benzenecarboperoxoic acid / 0 °C
5: 20 - 120 °C
View Scheme
Multi-step reaction with 5 steps
1: sodium carbonate / water / 4 h / 25 - 30 °C
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 5 °C
3: triethylamine / dichloromethane / 5 - 10 °C
4: sodium hydroxide / water / 8.17 h / 25 - 100 °C
5: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 14 h / 0 - 5 °C
View Scheme
Multi-step reaction with 5 steps
1: sodium carbonate; tetrabutylammomium bromide / water / 8 h / 25 - 30 °C
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 5 °C
3: triethylamine / dichloromethane / 5 - 10 °C
4: sodium hydroxide / water / 8.17 h / 25 - 100 °C
5: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 14 h / 0 - 5 °C
View Scheme
330785-81-4

ethyl 4-[(3-chloro-4-methoxybenzyl)amino]-2-(methylsulfanyl)pyrimidine-5-carboxylate

330784-47-9

avanafil

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydroxide / water; ethanol / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
3: 3-chloro-benzenecarboperoxoic acid / 0 °C
4: 20 - 120 °C
View Scheme
Multi-step reaction with 4 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 5 °C
2: triethylamine / dichloromethane / 5 - 10 °C
3: sodium hydroxide / water / 8.17 h / 25 - 100 °C
4: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 14 h / 0 - 5 °C
View Scheme
Multi-step reaction with 4 steps
1.1: water; sodium hydroxide / methanol / Reflux
2.1: thionyl chloride / toluene; N,N-dimethyl-formamide / 2.5 h / Reflux
2.2: 15 - 30 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 25 - 30 °C
4.1: triethylamine / dichloromethane
View Scheme
115514-77-7

(3-chloro-4-methoxyphenyl)methanamine

330784-47-9

avanafil

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: triethylamine / tetrahydrofuran / 20 °C
2: sodium hydroxide / water; ethanol / 20 °C
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
4: 3-chloro-benzenecarboperoxoic acid / 0 °C
5: 20 - 120 °C
View Scheme
Multi-step reaction with 6 steps
1: methanol / 0.25 h / 60 - 65 °C
2: sodium carbonate; tetrabutylammomium bromide / water / 8 h / 25 - 30 °C
3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 5 °C
4: triethylamine / dichloromethane / 5 - 10 °C
5: sodium hydroxide / water / 8.17 h / 25 - 100 °C
6: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 14 h / 0 - 5 °C
View Scheme
Multi-step reaction with 5 steps
1.1: tetrabutylammomium bromide; sodium carbonate / dichloromethane; water / 25 - 30 °C
2.1: water; sodium hydroxide / methanol / Reflux
3.1: thionyl chloride / toluene; N,N-dimethyl-formamide / 2.5 h / Reflux
3.2: 15 - 30 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 25 - 30 °C
5.1: triethylamine / dichloromethane
View Scheme
53554-29-3

ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate

330784-47-9

avanafil

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: trichlorophosphate / toluene / 4 h / 55 - 105 °C
2: sodium carbonate; tetrabutylammomium bromide / water / 8 h / 25 - 30 °C
3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 5 °C
4: triethylamine / dichloromethane / 5 - 10 °C
5: sodium hydroxide / water / 8.17 h / 25 - 100 °C
6: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 14 h / 0 - 5 °C
View Scheme
Multi-step reaction with 6 steps
1: trichlorophosphate / toluene / 4 h / 55 - 105 °C
2: sodium carbonate / water / 4 h / 25 - 30 °C
3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 5 °C
4: triethylamine / dichloromethane / 5 - 10 °C
5: sodium hydroxide / water / 8.17 h / 25 - 100 °C
6: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 14 h / 0 - 5 °C
View Scheme
Multi-step reaction with 6 steps
1: trichlorophosphate / acetonitrile / 6 h / Reflux
2: triethylamine / acetone / 3 h / 20 °C
3: methanol; sodium hydroxide / 4.5 h / 20 - 30 °C
4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide; N,N-dimethyl-aniline / 7 h / 60 °C
5: acetic acid; dihydrogen peroxide / 4 h / 65 - 80 °C
6: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 5 h / 20 °C
View Scheme
330785-82-5

4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonyl-2-methylsulfinylpyrimidine

330784-47-9

avanafil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 5 - 10 °C
2: sodium hydroxide / water / 8.17 h / 25 - 100 °C
3: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 14 h / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / -5 - 30 °C / Large scale
2: sodium hydroxide / dimethyl sulfoxide; water / 25 - 35 °C / Large scale
3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 - 25 °C
View Scheme

ethyl (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)tetrahydropyrrole-1-yl)-5-pyrimidinecarboxylate

330784-47-9

avanafil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 8.17 h / 25 - 100 °C
2: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 14 h / 0 - 5 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydroxide / water; dimethyl sulfoxide / 20 °C / Cooling with ice
2.1: triethylamine / N,N-dimethyl-formamide / 0.5 h
2.2: 8 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / water; dimethyl sulfoxide / 20 °C / Cooling with ice
2: thionyl chloride / 4 h / 80 °C
3: triethylamine / dichloromethane / 20 °C
View Scheme
372118-67-7

1-(pyrimidin-2-yl)methanamine hydrochloride

330785-84-7

4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidine-5-carboxylic acid

330784-47-9

avanafil

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 5℃; for 14h; Time;145 g

(3-chloro-4-methoxyphenyl)methanamine malate

330784-47-9

avanafil

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium carbonate; tetrabutylammomium bromide / water / 8 h / 25 - 30 °C
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 5 °C
3: triethylamine / dichloromethane / 5 - 10 °C
4: sodium hydroxide / water / 8.17 h / 25 - 100 °C
5: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 14 h / 0 - 5 °C
View Scheme

4-[(3-chloro-4-methoxybenzyl)amino]-2-(methyl sulfinyl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide

330784-47-9

avanafil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / dichloromethane
2.1: sulfuric acid / ethanol / Reflux
2.2: 5 h
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / dichloromethane
2.1: thionyl chloride / toluene; N,N-dimethyl-formamide / 2.5 h / Reflux
3.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 5 °C
3.2: 60 - 70 °C
View Scheme

4-[(3-chloro-4-methoxybenzyl)amino]-2-(methyl sulfinyl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide

23356-96-9

(S)-1-Pyrrolidin-2-yl-methanol

330784-47-9

avanafil

Conditions
ConditionsYield
With triethylamine In dichloromethane8 g

C23H24ClN7O4

330784-47-9

avanafil

Conditions
ConditionsYield
Stage #1: C23H24ClN7O4 With sulfuric acid In ethanol Reflux;
Stage #2: With sodium tetrahydroborate; lithium bromide In ethanol for 5h;
7.5 g

C23H23Cl2N7O3

330784-47-9

avanafil

Conditions
ConditionsYield
Stage #1: C23H23Cl2N7O3 With sodium tetrahydroborate In tetrahydrofuran at 0 - 5℃;
Stage #2: With potassium hydroxide In water at 60 - 70℃;
40 g
320407-92-9

4-(bromomethyl)-2-chloro-1-methoxybenzene

330784-47-9

avanafil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium iodide; triethylamine / ethanol / 3 h / 50 - 80 °C
2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 24 h / 20 - 60 °C / Inert atmosphere
2.2: 5 h / 55 °C
3.1: bromine; sodium hydroxide / 0.08 h / Microwave irradiation
3.2: 10 h / 120 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: potassium iodide; triethylamine / ethanol / 3 h / 50 - 80 °C
2.1: sodium hydroxide; iodine / 0.08 h / Microwave irradiation
2.2: 10 h / 110 °C / Inert atmosphere
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 24 h / 20 - 60 °C / Inert atmosphere
3.2: 5 h / 65 °C
View Scheme
330784-47-9

avanafil

77-92-9

citric acid

avanafil-citric acid

Conditions
ConditionsYield
In acetone at 25℃; for 8h; Solvent; Sealed tube;96.5%
330784-47-9

avanafil

4-nitrophenyl 3-[(25)-2,3-bis(nitrooxy)propoxy] propanoate

[(2S)-1-(4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-5-{[(pyrimidin-2-yl)methyl]carbamoyl}pyrimidin-2-yl)pyrrolidin-2-yl]methyl 3-[(2S)-2,3-bis(nitrooxy)propoxy]propanoate

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃;95%
330784-47-9

avanafil

1178531-55-9

(5S)-5,6-bis(nitrooxy)hexanoic acid

[(2S)-1-(4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-5-{[(pyrimidin-2-yl)methyl]carbamoyl}pyrimidin-2-yl)pyrrolidin-2-yl]methyl (5S)-5,6-bis(nitrooxy)hexanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;94.5%
330784-47-9

avanafil

74754-55-5

6-(nitrooxy)hexanoic acid

(S)-(1-(4-(3-chloro-4-methoxybenzylamino)-5-(pyrimidin-2-ylmethylcarbamoyl)pyrimidin-2-yl)pyrrolidin-2-yl)methyl 6-(nitrooxy)hexanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;93%
330784-47-9

avanafil

1321458-84-7

2-(2-(nitrooxy)ethoxy)acetic acid

(S)-(1-(4-(3-chloro-4-methoxybenzylamino)-5-(pyrimidin-2-ylmethylcarbamoyl)pyrimidin-2-yl)pyrrolidin-2-yl)methyl 2-(2-(nitrooxy)ethoxy)acetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;52%
330784-47-9

avanafil

19961-29-6

boron monobromide

144-55-8

sodium hydrogencarbonate

330785-05-2

(S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-hydroxybenzylamino)-5-[N-(2-pyrimidylmethyl)carbamoyl]pyrimidine

Conditions
ConditionsYield
In tetrahydrofuran; methanol; dichloromethane; chloroform; ethyl acetate
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Specification

The Avanafil with the CAS number 330784-47-9 is also called 5-Pyrimidinecarboxamide,4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-N-(2-pyrimidinylmethyl)-. The IUPAC name is 4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide. Its molecular formula is C23H26ClN7O3. The classification code is Treatment of erectile dysfunction.

The properties of the Avanafil are: (1)ACD/LogP: 1.84; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 0; (4)ACD/LogD (pH 7.4): 1; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 6; (7)ACD/KOC (pH 5.5): 9; (8)ACD/KOC (pH 7.4): 124; (9)#H bond acceptors: 10; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 125.39 Å2; (13)Index of Refraction: 1.651; (14)Molar Refractivity: 128.832 cm3; (15)Molar Volume: 352.588 cm3; (16)Polarizability: 51.073×10-24cm3; (17)Surface Tension: 69.965 dyne/cm.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1c(OC)ccc(c1)CNc3nc(ncc3C(=O)NCc2ncccn2)N4[C@@H](CCC4)CO
(2)InChI: InChI=1/C23H26ClN7O3/c1-34-19-6-5-15(10-18(19)24)11-27-21-17(22(33)28-13-20-25-7-3-8-26-20)12-29-23(30-21)31-9-2-4-16(31)14-32/h3,5-8,10,12,16,32H,2,4,9,11,13-14H2,1H3,(H,28,33)(H,27,29,30)/t16-/m0/s1
(3)InChIKey: WEAJZXNPAWBCOA-INIZCTEOBD

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