2,4(1H,3H)-Pyrimidinedione, 3-((2R)-2-amino-2-phenylethyl)-1-((2,6-difluorophenyl)methyl)-5-(2-fluoro-3-methoxyphenyl)-6-methyl-

Base Information

• Chemical Name: 2,4(1H,3H)-Pyrimidinedione, 3-((2R)-2-amino-2-phenylethyl)-1-((2,6-difluorophenyl)methyl)-5-(2-fluoro-3-methoxyphenyl)-6-methyl-
• CAS No.: 352290-60-9
• Molecular Formula: C27H24F3N3O3
• Molecular Weight: 495.501
• UNII: 3FWQ4MD98O
• Wikidata: Q27087859
• Pharos Ligand ID: JLV6KFNGSRZS
• ChEMBL ID: CHEMBL179691
• Mol file: 352290-60-9.mol

Synonyms:1-(2,6-difluuorobenzyl)-3-((2R)-amino-2-phenethyl)-5-(2-fluoro-3-methoxyphenyl)-6-methyluracil;3-(2-amino-2-phenylethyl)-1-(2,6-difluorobenzyl)-5-(2-fluoro-3-methoxyphenyl)-6-methylpyrimidin-2,4-dione;NBI 42902;NBI-42902;NBI42902

Chemical Property of 2,4(1H,3H)-Pyrimidinedione, 3-((2R)-2-amino-2-phenylethyl)-1-((2,6-difluorophenyl)methyl)-5-(2-fluoro-3-methoxyphenyl)-6-methyl-

Chemical Property:

• PSA: 79.25000
• LogP: 4.85990
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 495.17697612
• Heavy Atom Count: 36
• Complexity: 824

Purity/Quality:

99% ^*data from raw suppliers

NBI42902 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(=O)N(C(=O)N1CC2=C(C=CC=C2F)F)CC(C3=CC=CC=C3)N)C4=C(C(=CC=C4)OC)F
• Isomeric SMILES: CC1=C(C(=O)N(C(=O)N1CC2=C(C=CC=C2F)F)C[C@@H](C3=CC=CC=C3)N)C4=C(C(=CC=C4)OC)F

Technology Process of 2,4(1H,3H)-Pyrimidinedione, 3-((2R)-2-amino-2-phenylethyl)-1-((2,6-difluorophenyl)methyl)-5-(2-fluoro-3-methoxyphenyl)-6-methyl-

There total 5 articles about 2,4(1H,3H)-Pyrimidinedione, 3-((2R)-2-amino-2-phenylethyl)-1-((2,6-difluorophenyl)methyl)-5-(2-fluoro-3-methoxyphenyl)-6-methyl- 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:

3-[2(R)-(tert-butoxycarbonylamino)-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2,6-difluorobenzyl]-6-methylpyrimidine-2,4(1H,3H)-dione (830346-53-7) → [3H]-NBI-42902 (352290-60-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃;

DOI:10.1021/jm049218c

Reference yield:

(R)-N-(tert-butoxycarbonyl)phenylglycinol (67341-01-9,117049-14-6,138457-46-2,102089-74-7) → [3H]-NBI-42902 (352290-60-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 55 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 16 h / 20 °C

2: aq. Ba(OH)2; tetrakis(triphenylphosphine)palladium / benzene; ethanol; 1,2-dimethoxy-ethane / 15 h / 80 °C

3: 1.32 g / TFA / CH₂Cl₂ / 20 °C

With barium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; benzene; 1: Mitsunobu reaction / 2: Suzuki coupling;

DOI:10.1021/jm049218c

Reference yield:

5-bromo-1-(2,6-difluoro-benzyl)-6-methyl-1H-pyrimidine-2,4-dione (352303-66-3) → [3H]-NBI-42902 (352290-60-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 55 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 16 h / 20 °C

2: aq. Ba(OH)2; tetrakis(triphenylphosphine)palladium / benzene; ethanol; 1,2-dimethoxy-ethane / 15 h / 80 °C

3: 1.32 g / TFA / CH₂Cl₂ / 20 °C

With barium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; benzene; 1: Mitsunobu reaction / 2: Suzuki coupling;

DOI:10.1021/jm049218c

upstream raw materials:

3-[2(R)-(tert-butoxycarbonylamino)-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2,6-difluorobenzyl]-6-methylpyrimidine-2,4(1H,3H)-dione

(R)-N-(tert-butoxycarbonyl)phenylglycinol

5-bromo-1-(2,6-difluoro-benzyl)-6-methyl-1H-pyrimidine-2,4-dione

{(R)-2-[5-bromo-3-(2,6-difluoro-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester

Downstream raw materials:

3-[2(R)-(tert-butoxycarbonylamino)-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2,6-difluorobenzyl]-6-methylpyrimidine-2,4(1H,3H)-dione

Refernces

• 1、 Tucci, Fabio C.,Zhu, Yun-Fei,Struthers, R. Scott,Guo, Zhiqiang,Gross, Timothy D.,Rowbottom, Martin W.,Acevedo, Oscar,Gao, Yinghong,Saunders, John,Xie, Qiu,Reinhart, Greg J.,Liu, Xin-Jun,Ling, Nicholas,Bonneville, Anne K. L.,Chen, Takung,Bozigrian, Haig,Chen, Chen. "3-[(2R)-amino-2-phenylethyl]-1-(2,6-difluorobenzyl)-5-(2-fluoro-3- methoxyphenyl)-6-methylpyrimidin-2,4-dione (NBI 42902) as a potent and orally active antagonist of the human gonadotropin-releasing hormone receptor. Design, synthesis, and in vitro and in vivo characterization". . p. 1169 - 1178. Retrieved 2007/10/03.
• 2、 -. "PYRIMIDINE-2, 4-DIONE DERIVATIVES AS GONADOTROPIN-RELEASING HORMONE RECEPTOR ANTAGONISTS". Page 28-29. . Retrieved 2010/02/10.