| Identification | Back Directory | [Name]
(5-PyriMidinecarboxylicacid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-(Methylthio)-,ethyl ester) | [CAS]
330785-81-4 | [Synonyms]
Avanafil Intermediate II
INTERMEDIATE OF AVANAFIL
4-(3-chloro-4-MethoxybenzylaMino)-5-ethoxycarbonyl-2-MethylthiopyriMidine
ethyl 4-(3-chloro-4-MethoxybenzylaMino)-2-(Methylthio)pyriMidine-5-carboxylate
ethyl 4-[(3-chloro-4-methoxyphenyl)methylamino]-2-methylsulfanylpyrimidine-5-carboxylate
4-(3-Chloro-4-Methoxy-benzylaMino)-2-Methylsulfanyl-pyriMidine-5-carboxylic acid ethyl ester
4-[[(3-Chloro-4-methoxyphenyl)methyl]amino]-2-(methylthio)-5-pyrimidinecarboxylic acid ethyl ester
(5-PyriMidinecarboxylicacid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-(Methylthio)-,ethyl ester)
(5-PyriMidinecarboxylicacid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-(Methylthio)-,ethyl ester)###NA
Avanafil intermediates，5-Pyrimidinecarboxylicacid, 4-[[(3- chloro-4- methoxyphenyl)methyl]amino]-2- (methylthio)-, ethyl ester
Ethyl 4-[(3-chloro-4-methoxybenzyl)amino]-2-(methylsulphanyl)pyrimidine-5-carboxylate, 4-[(3-Chloro-4-methoxybenzyl)amino]-5-(ethoxycarbonyl)-2-(methylthio)pyrimidine | [EINECS(EC#)]
801-713-7 | [Molecular Formula]
C16H18ClN3O3S | [MDL Number]
MFCD17012695 | [MOL File]
330785-81-4.mol | [Molecular Weight]
367.85 |
| Chemical Properties | Back Directory | [Boiling point ]
514.9±45.0 °C(Predicted) | [density ]
1.33±0.1 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | [form ]
powder | [pka]
2.70±0.10(Predicted) | [color ]
White | [InChI]
InChI=1S/C16H18ClN3O3S/c1-4-23-15(21)11-9-19-16(24-3)20-14(11)18-8-10-5-6-13(22-2)12(17)7-10/h5-7,9H,4,8H2,1-3H3,(H,18,19,20) | [InChIKey]
WLOQDGSMJNYRRC-UHFFFAOYSA-N | [SMILES]
C1(SC)=NC=C(C(OCC)=O)C(NCC2=CC=C(OC)C(Cl)=C2)=N1 |
| Hazard Information | Back Directory | [Uses]
4-(3-Chloro-4-methoxybenzylamino)-5-ethoxycarbonyl-2-methylthiopyrimidine is an intermediate for Avanafil (A794670) derivatives. Avanafil is a phosphodiesterase (PDE5) inhibitor, used to treat erectile dysfunction. | [Synthesis]
General procedure for the synthesis of 4-(3-chloro-4-methoxybenzylamino)-2-methylmercapto-5-ethoxycarbonylpyrimidine from 4-chloro-2-methylthiopyrimidine-5-carboxylic acid ethyl ester and 3-chloro-4-methoxybenzylamine: firstly, 3-chloro-4-methoxybenzylamine (45.6 g, 0.27 mol) was dissolved in 180 mL of acetone, followed by triethylamine (40.4 g, 0.4 mol). Next, ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate (53.3 g, 0.24 mol) was dissolved in 250 mL of acetone and slowly added dropwise to the above reaction solution. The reaction was carried out at room temperature for 3 hours. Upon completion of the reaction, the reaction solution was poured into an ice-water mixture and extracted with ethyl acetate. The organic phases were combined and washed with 10% aqueous citric acid (250 mL x 3). The organic layer was dried with anhydrous sodium sulfate, followed by evaporation of the solvent under reduced pressure. Finally, the product was dried under vacuum to give a white solid (86.0 g, 87.0% yield). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 23, p. 5460 - 5465
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 7, p. 1431 - 1435
[3] Patent: CN108707141, 2018, A. Location in patent: Paragraph 0027; 0031; 0036; 0040; 0045; 0049
[4] Patent: EP2886540, 2015, A1. Location in patent: Paragraph 0168; 0169
[5] Patent: EP1366760, 2003, A1. Location in patent: Page 19 |
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