2-(N,N-Bisboc-amino)pyrimidine-5-boronic acid, pinacol ester

Base Information

• Chemical Name: 2-(N,N-Bisboc-amino)pyrimidine-5-boronic acid, pinacol ester
• CAS No.: 1190423-36-9
• Molecular Formula: C20H32BN3O6
• Molecular Weight: 421.302
• Hs Code.: 2933599590
• European Community (EC) Number: 830-721-3
• DSSTox Substance ID: DTXSID50475067
• Wikidata: Q82305322
• Mol file: 1190423-36-9.mol

Synonyms:1190423-36-9;2-(N,N-BISBOC-AMINO)PYRIMIDINE-5-BORONIC ACID, PINACOL ESTER;tert-butyl N-[(2-methylpropan-2-yl)oxycarbonyl]-N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]carbamate;tert-butyl N-[(tert-butoxy)carbonyl]-N-[5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]carbamate;Imidodicarbonic acid, 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyrimidinyl]-, 1,3-bis(1,1-dimethylethyl) ester;SCHEMBL799138;C20H32BN3O6;DTXSID50475067;SJJXYKAZGIJVQP-UHFFFAOYSA-N;MFCD12913985;AKOS015999376;SB55509;DS-17489;CS-0041073;EN300-246322;F20523;A892676;J-506509;Z2044826974;2-(N,N-BisBOC-Amino)pyrimidine-5-boronic acid pinacol ester;Di-tert-butyl [5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]-2-imidodicarbonate;di-tert-butyl[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]imidodicarbonate;tert-Butyl (tert-butoxycarbonyl)(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)carbamate

Chemical Property of 2-(N,N-Bisboc-amino)pyrimidine-5-boronic acid, pinacol ester

Chemical Property:

• Boiling Point: 498.3±37.0 °C(Predicted)
• PKA: -0.76±0.10(Predicted)
• PSA: 100.08000
• Density: 1.15±0.1 g/cm3(Predicted)
• LogP: 3.45240
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 421.2384159
• Heavy Atom Count: 30
• Complexity: 604

Purity/Quality:

98%min ^*data from raw suppliers

2-(N,N-BisBOC-Amino)pyrimidine-5-boronicAcid,PinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN=C(N=C2)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C
• Uses: 2-(N,N-BisBOC-Amino)pyrimidine-5-boronic Acid, Pinacol Ester acts as a reagent in the synthesis of pyrrolotriazine derivatives as PI3 kinase inhibitor, preparation of heteroaryl carbazoles as inhibitors of Hsp82 and Hsp90 proteins for treating cancer.

Technology Process of 2-(N,N-Bisboc-amino)pyrimidine-5-boronic acid, pinacol ester

There total 3 articles about 2-(N,N-Bisboc-amino)pyrimidine-5-boronic acid, pinacol ester 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: 54.0%

→ bis(2-methylpropan-2-yl) [5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]imidodicarbonate (1190423-36-9)

Guidance literature:

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (1173206-16-0) → bis(2-methylpropan-2-yl) [5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]imidodicarbonate (1190423-36-9)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 15h;

Reference yield:

2-(di-(tert-butoxycarbonyl)amino)pyrimidine (264600-82-0) + bis(pinacol)diborane (73183-34-3) → bis(2-methylpropan-2-yl) [5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]imidodicarbonate (1190423-36-9)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin; In tetrahydrofuran; at 80 ℃; for 24h; Glovebox; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.9b03296

upstream raw materials:

di-tert-butyl dicarbonate

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine

2-(di-(tert-butoxycarbonyl)amino)pyrimidine

bis(pinacol)diborane

Downstream raw materials:

5-{3-[4-(1-aminocyclobutyl)phenyl]-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-2-yl}pyrimidin-2-amine

C₃₃H₃₀FN₅O₄

2-methylpropan-2-yl [5-(9-{4-carbamoyl-3-[(4-trans-hydroxycyclohexyl)amino]phenyl}-9H-carbazol-4-yl)pyrimidin-2-yl]carbamate

Refernces

• 1、 -. "NOVEL HSP90 INHIBITORY CARBAZOLE DERIVATIVES, COMPOSITIONS CONTAINING SAME AND USE THEREOF". Page/Page column 67. . Retrieved 2011/07/29.