2,4-Bis(benzyloxy)pyrimidine-5-boronic acid

Base Information

• Chemical Name: 2,4-Bis(benzyloxy)pyrimidine-5-boronic acid
• CAS No.: 70523-24-9
• Molecular Formula: C18H17 B N2 O4
• Molecular Weight: 336.155
• Hs Code.: 29310095
• DSSTox Substance ID: DTXSID90370764
• Nikkaji Number: J1.592.977D
• Wikidata: Q72444284
• Mol file: 70523-24-9.mol

Synonyms:70523-24-9;2,4-BIS(BENZYLOXY)PYRIMIDINE-5-BORONIC ACID;2,4-bis(benzyloxy)pyrimidin-5-ylboronic acid;[2,4-bis(phenylmethoxy)pyrimidin-5-yl]boronic Acid;(2,4-bis(benzyloxy)pyrimidin-5-yl)boronic acid;2,4-Bis(benzyloxy)pyrimidin-5-ylboronic acid;2,4-Bis(benzyloxy)pyrimidine-5-boronic acid;[2,4-bis(benzyloxy)pyrimidin-5-yl]boronic acid;C18H17BN2O4;[2,4-BIS(PHENYLMETHOXY)-5-PYRIMIDINYL]-BORONIC ACID;SCHEMBL2724131;AMY7877;DTXSID90370764;HVVGEQHZGHNHJD-UHFFFAOYSA-N;MFCD01318938;AKOS004116212;AB08761;AC-7000;PS-9668;2,4-Dibenzyloxypyrimidine-5-boronic acid;A9297;FT-0605406;2,4-Bis(benzyloxy)pyrimidine-5-ylboronic acid;E89564;2,4-bis(benzyloxy)pyrimidine-5-boronic acid, AldrichCPR;2-Amino-pyrrolidine-1-carboxylic?acid?tert-butyl?ester;F0001-1826

Chemical Property of 2,4-Bis(benzyloxy)pyrimidine-5-boronic acid

Chemical Property:

• Vapor Pressure: 2.88E-15mmHg at 25°C
• Melting Point: 88-91℃
• Boiling Point: 600.4 ºC at 760 mmHg
• Flash Point: 316.9 ºC
• PSA: 84.70000
• Density: 1.3 g/cm³
• LogP: 1.31440
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 336.1281372
• Heavy Atom Count: 25
• Complexity: 376

Purity/Quality:

99% ^*data from raw suppliers

2,4-Bis(benzyloxy)pyrimidine-5-boronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CN=C(N=C1OCC2=CC=CC=C2)OCC3=CC=CC=C3)(O)O
• Uses: 2,4-Bis(benzyloxy)pyrimidine-5-boronic Acid is used as a reactant in the design and synthesis of acyclic fleximer nucleoside analogues.

Technology Process of 2,4-Bis(benzyloxy)pyrimidine-5-boronic acid

There total 3 articles about 2,4-Bis(benzyloxy)pyrimidine-5-boronic acid 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: 95.0%

5-bromo-2,4-bis(benzyloxy)pyrimidine (41244-53-5) → 5-(dihydroxyboryl)-2,4-bis(benzyloxy)pyrimidine (70523-24-9)

Guidance literature:

5-bromo-2,4-bis(benzyloxy)pyrimidine; With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; hexane; toluene; at 20 ℃; for 18h;

With hydrogenchloride; In tetrahydrofuran; hexane; toluene;

DOI:10.1021/jo048218h

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → 5-(dihydroxyboryl)-2,4-bis(benzyloxy)pyrimidine (70523-24-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 91 percent / NaH / various solvent(s); toluene / 18 h / 20 °C

2.1: n-butyllithium; B(OiPr)3 / hexane; tetrahydrofuran; toluene / 18 h / 20 °C

2.2: 95 percent / aq.HCl / toluene; tetrahydrofuran; hexane

With n-butyllithium; Triisopropyl borate; sodium hydride; In tetrahydrofuran; hexane; toluene;

DOI:10.1021/jo048218h

Reference yield:

→ 5-(dihydroxyboryl)-2,4-bis(benzyloxy)pyrimidine (70523-24-9)

Guidance literature:

5-Bromo-2,4-dibenzoylpyrimidin(3),Borierung;

DOI:10.1016/S0040-4039(01)85787-7

upstream raw materials:

5-bromo-2,4-bis(benzyloxy)pyrimidine

benzyl alcohol

Downstream raw materials:

2,4-bis(benzyloxy)-5-1-[(3,5-di-O-benzyl-2-deoxy-β-D-ribofuranosyl)-1H-imidazol-4-yl]pyrimidine

5-[3-(2-Amino-pyrimidin-4-yl)-4-hydroxy-phenyl]-1 H-pyrimidine-2.4-dione

2,4-Bis-benzyloxy-5-[1-((2R,3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-imidazol-4-yl]-pyrimidine

Refernces

• 1、 Seley, Katherine L.,Salim, Samer,Zhang, Liang,O'Daniel, Peter I.. ""Molecular chameleons". Design and synthesis of a second series of flexible nucleosides". . p. 1612 - 1619. Retrieved 2007/10/03.