2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine

Base Information

• Chemical Name: 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine
• CAS No.: 209959-33-1
• Molecular Formula: C14H20 Br N3 O4
• Molecular Weight: 374.234
• European Community (EC) Number: 696-598-1
• DSSTox Substance ID: DTXSID90475066
• Nikkaji Number: J2.362.822H
• Wikidata: Q72512225
• Mol file: 209959-33-1.mol

Synonyms:209959-33-1;2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine;2-(N,N-BisBOC-Amino)-5-bromopyrimidine;tert-butyl N-(5-bromopyrimidin-2-yl)-N-[(tert-butoxy)carbonyl]carbamate;Tert-butyl N-(5-bromopyrimidin-2-yl)-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate;MFCD08275685;2-[N,N-bis(tert-butoxycarbonyl)amino)-5-bromopyrimidin;2-[N,N-bis(tert-butoxycarbonyl)amino]-5-bromopyrimidin;C14H20BrN3O4;SCHEMBL2378220;DTXSID90475066;GDKYABNFMXOTAN-UHFFFAOYSA-N;AKOS015836762;SB18486;SS-4436;CS-0048062;FT-0655778;N,N-BIS-BOC-2-AMINO-5-BROMOPYRIMIDINE;A815066;n,n-di-t-butoxycarbonyl-5-bromopyrimidin-2-amine;Di-tert-butyl (5-bromopyrimidin-2-yl)-2-imidodicarbonate;tert-Butyl N-(5-bromopyrimidin-2-yl)-N-[(tert-butoxy)carbonyl]carbamate, AldrichCPR;tert-butyl N-(5-bromopyrimidin-2-yl)-N-tert-butoxycarbonyl-carbamate

Chemical Property of 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 415.197oC at 760 mmHg
• PKA: -2.49±0.10(Predicted)
• Flash Point: 204.904oC
• PSA: 81.62000
• Density: 1.39g/cm3
• LogP: 3.91570
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 373.06372
• Heavy Atom Count: 22
• Complexity: 381

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N(C1=NC=C(C=N1)Br)C(=O)OC(C)(C)C

Technology Process of 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine

There total 2 articles about 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine 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: 93.0%

5-bromo-2-aminopyrimidine (7752-82-1) + di-tert-butyl dicarbonate (24424-99-5) → 2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine (209959-33-1)

Guidance literature:

With pyridine; at 70 ℃;

Reference yield: 72.0%

di-tert-butyl dicarbonate (24424-99-5) → 2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine (209959-33-1)

Guidance literature:

In tetrahydrofuran; 5-bromo-2-aminopyrimidine;

Reference yield: 96.0%

2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine (209959-33-1) + (2-methylsulfanylphenyl)boronic acid (168618-42-6) → 2-[Bis(tert-butoxycarbonyl)amino]-5-(2'-methylthiophenyl)-pyrimidine

Guidance literature:

With tetrabutylammomium bromide; sodium carbonate; bis-triphenylphosphine-palladium(II) chloride; In water; benzene; for 17h; Reflux;

upstream raw materials:

5-bromo-2-aminopyrimidine

di-tert-butyl dicarbonate

Downstream raw materials:

2-(5-hydroxy-2-pyrimidinyl)imidodicarbonic acid 1,3-bis(1,1-dimethylethyl)ester

tert-butyl (5-bromopyrimidin-2-yl)carbamate

Refernces

• 1、 -. "Compounds for treating spinal muscular atrophy". Page/Page column 371. . Retrieved 2017/05/02.
• 2、 Hoang, Van-Hai,Tran, Phuong-Thao,Cui, Minghua,Ngo, Van T. H.,Ann, Jihyae,Park, Jongmi,Lee, Jiyoun,Choi, Kwanghyun,Cho, Hanyang,Kim, Hee,Ha, Hee-Jin,Hong, Hyun-Seok,Choi, Sun,Kim, Young-Ho,Lee, Jeewoo. "Discovery of Potent Human Glutaminyl Cyclase Inhibitors as Anti-Alzheimer’s Agents Based on Rational Design". . p. 2573 - 2590. Retrieved 2017/04/03.