Tert-butyl (5-bromopyrimidin-2-YL)carbamate

Base Information

• Chemical Name: Tert-butyl (5-bromopyrimidin-2-YL)carbamate
• CAS No.: 883231-23-0
• Molecular Formula: C9H12BrN3O2
• Molecular Weight: 274.12
• Hs Code.: 2933599090
• DSSTox Substance ID: DTXSID40595026
• Wikidata: Q72502598
• Mol file: 883231-23-0.mol

Synonyms:883231-23-0;N-Boc-2-Amino-5-bromopyrimidine;TERT-BUTYL (5-BROMOPYRIMIDIN-2-YL)CARBAMATE;2-(N-BOC-Amino)-5-bromopyrimidine;tert-butyl N-(5-bromopyrimidin-2-yl)carbamate;5-Bromo-N-Boc-Pyrimidin-2-Amine;MFCD13188600;t-Butyl 5-bromopyrimidin-2-ylcarbamate;SCHEMBL15635115;DTXSID40595026;MQQCCIJHZDEZBW-UHFFFAOYSA-N;AMY10264;AKOS015838243;CS-W007068;DS-12768;SY105495;tert-Butyl 5-bromopyrimidin-2-ylcarbamate;tert-Butyl (5-bromo-2-pyrimidinyl)carbamate;F20486;EN300-1877906

Chemical Property of Tert-butyl (5-bromopyrimidin-2-YL)carbamate

Chemical Property:

• PKA: 10.38±0.70(Predicted)
• PSA: 67.60000
• Density: 1.513 g/cm³
• LogP: 2.59970
• Storage Temp.: Room temperature.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 273.01129
• Heavy Atom Count: 15
• Complexity: 222

Purity/Quality:

98%min ^*data from raw suppliers

2-(N-BOC-Amino)-5-bromopyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1=NC=C(C=N1)Br

Technology Process of Tert-butyl (5-bromopyrimidin-2-YL)carbamate

There total 2 articles about Tert-butyl (5-bromopyrimidin-2-YL)carbamate 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: 90.0%

5-bromo-2-aminopyrimidine (7752-82-1) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (5-bromopyrimidin-2-yl)carbamate (883231-23-0)

Guidance literature:

5-bromo-2-aminopyrimidine; di-tert-butyl dicarbonate; With dmap; triethylamine; In N,N-dimethyl-formamide; at 60 ℃; for 5h;

With potassium carbonate; In methanol; at 60 ℃; for 1.5h;

DOI:10.1016/j.ejmech.2015.11.038

Reference yield:

2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine (209959-33-1) → tert-butyl (5-bromopyrimidin-2-yl)carbamate (883231-23-0)

Guidance literature:

With sodium hydroxide; In ethanol; water;

Reference yield: 30.0%

tert-butyl (5-bromopyrimidin-2-yl)carbamate (883231-23-0) + m-nitrobenzene boronic acid (13331-27-6) → tert-butyl (5-(3-nitrophenyl)pyrimidin-2-yl)carbamate

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In tetrahydrofuran; for 20h; Inert atmosphere; Reflux;

DOI:10.1039/d0md00238k

upstream raw materials:

2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine

5-bromo-2-aminopyrimidine

di-tert-butyl dicarbonate

Downstream raw materials:

tert-butyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]carbamate

Refernces

• 1、 -. "PROCESS FOR MAKING THIENOPYRIMIDINE COMPOUNDS". Page/Page column. . Retrieved 2014/04/18.