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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)-
Article Data: 20
Cas Database
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: 483.958
Synonyms: (S)-2-(2-Hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[(2-pyrimidinylmethyl)carbamoyl]pyrimidine;TA 1790;
EINECS: N/A
Density: 1.373 g/cm3
Melting Point: 150-152 °C
Boiling Point: N/A
Flash Point: N/A
Solubility: N/A
Appearance: White solid
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
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%
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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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